9: (yellow oil); 1H NMR (400 MHz, CDCl3): δ = 3.74 (s, 4H), 3.85 (t, J = 4.4 Hz, 4H), 4.10 (t, J = 4.4 Hz,
4H), 4.49 (d, J = 5.2 Hz, 4H), 5.25-5.41 (m, 4H), 5.99-6.08 (m, 2H), 6.47-6.54 (m, 6H), 7.14 (t, J = 8 Hz,
2H); 13C NMR (100 MHz, CDCl3): δ = 67.54, 68.95, 69.93, 71.02, 102.03, 107.14, 107.40, 117.82,
129.98, 133.40, 159.93, 160.13; HRMS (Q-Tof) m/z: [M+Na]+ calcd. for C24H30O6K 453.1671, found
453.1674;IR (neat): υmax: 740, 1265, 1453, 1598, 2873, 3054 cm-1.
1
12: (yellow oil); H NMR (400 MHz, CDCl3): δ = 3.70 (s, 4H), 3.83 (t, J = 5.3 Hz, 4H), 4.07 (t, J = 5.3
13
Hz, 4H), 4.46 (td, J1 = 1.1 Hz, J2 = 5.3 Hz, 4H), 5.24-5.41 (m, 4H), 5.99-6.08 (m, 2H), 6.83 (s, 8H); C
NMR (100 MHz, CDCl3): δ = 68.21, 69.61, 70.06, 71.00, 115.74, 115.79, 117.65, 133.74, 153.06,
153.22; HRMS (Q-Tof) m/z: [M+Na]+ calcd. for C24H30O6Na 437.1943, found 437.1935; IR (neat): υmax
:
743, 1112, 1229, 1265, 1456, 1506, 2987, 3054 cm-1.
General procedure for Claisen rearrangement
Product obtained by allylation (3, 9, or 12) (1 mmol) was dissolved in dichlorobenzene (10 mL) and
reaction mixture was heated at reflux for a period of 24 h After completion of the reaction (TLC
monitoring), reaction mixture was cooled. Crude reaction mixture was directly subjected to column
chromatography. Dichlorobenzene was removed by elution with petroleum ether. Further elution of
compound was done by using petroleum ether/ethyl acetate mixture.
1
6: (colourless oil); H NMR (400 MHz, CDCl3): δ = 3.43 (d, J = 6.7 Hz, 4H), 3.82-3.84 (m, 4H), 4.17-
4.19 (m, 4H), 5.02-5.10 (m, 4H), 5.97-6.07 (m, 2H), 6.74-7.24 (m, 6H), 7.28 (s, 2H); 13C NMR (100
MHz, CDCl3): δ = 34.16, 69.64, 69.83, 113.51, 115.54, 119.51, 124.00, 127.53, 136.96, 145.37, 145.71;
HRMS (Q-Tof) m/z: [M+Na]+ calcd. for C22H26O5Na 393.1674, found 393.1672; IR (neat): υmax: 736,
1265, 1455, 1586, 2935, 2984, 3690 cm-1.
10a: (colourless oil); 1H NMR (400 MHz, CDCl3): δ = 3.45 (d, J = 6.2 Hz, 4H), 3.74 (s, 4H), 3.85 (t, J =
4.7 Hz, 4H), 4.10 (t, J = 4.7 Hz, 4H), 5.91-6.00 (m, 2H), 6.41-6.50 (m, 4H), 6.46 (dd, J1 = 2.9 Hz, J2 = 8.3
Hz, 4H), 7.02 (t, J = 8.0 Hz, 2H); 13C NMR (100 MHz, CDCl3): δ = 27.73, 68.34, 70.05, 71.13, 104.74,
109.20, 114.33, 115.58, 127.66, 136.60, 155.38, 157.56; HRMS (Q-Tof) m/z: [M+Na]+ calcd. for
C24H30O6Na 437.1935, found 437.1931; IR (neat): υmax: 728, 1268, 1422, 1596, 2927, 2986, 3584 cm-1.
1
13: (colourless oil); H NMR (400 MHz, CDCl3): δ = 3.33 (d, J = 6.0 Hz, 4H), 3.72 (s, 4H), 3.82 (t, J =
6.0 Hz, 4H), 4.03 (t, J = 6.0 Hz, 4H), 5.01 (bs, 2H), 5.09-5.14 (m, 4H), 5.90-6.01 (m, 2H), 6.61-6.72 (m,
6H); 13C NMR (100 MHz, CDCl3): δ = 35.30, 68.10, 70.09, 70.95, 113.55, 116.52, 116.61, 117.02,
126.70, 136.39, 148.34, 152.94; HRMS (Q-Tof) m/z: [M+Na]+ calcd. for C24H30O6Na 437.1935, found
437.1943; IR (neat): υmax: 749, 1262, 1422, 1506, 2987, 3055, 3689 cm-1.
8