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9. Typical procedure (Table 1, entry 11–2): Resin 3 (5 g, 5.4
mmol, loading: 1.08 mmol/g; purchased from Argonaut
Technologies) was treated with cyclohexanone (10.6 g,
108 mmol, 20 equiv.) and p-TsOH (40 mg, 0.21 mmol) in
benzene (80 mL). The reaction mixture was refluxed for
,
24 h using 4 A molecular sieve containing Dean–Stark
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apparatus under nitrogen. The resin was washed with
dried benzene (30 mL×5) under nitrogen, and put under
vacuum to afford 5.4 g of desired resin 7 (n=2) (FTIR
(KBr): 1682 cm−1). To the suspension of resin 7 (n=2) (1
g, 1 mmol/g) in DCM (20 mL) was added Et3N (2 mmol,
0.28 mL), followed by the addition of 2-chlorobenzoyl
chloride (2 mmol, 0.18 g). The reaction mixture was
stirred at rt overnight. The resin was filtered, washed with
DCM (20 mL×3), and treated with THF/1N HCl (6
mL/1 mL) for 20 min at rt. After filtration of the resin,
the filtrate was concentrated under Genvac to afford enol
ester 10 (n=2), which was finally saponified (THF/1N
NaOH=6 mL/1 mL) at rt for 4 h. Sequential neutraliza-
tion (1N HCl, pH 7), concentration under Genvac, and
short silica column chromatography afforded 1,3-dike-
tone 11-2 as a white solid (150 mg). Yield (overall): 66%,
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INORG-080.
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6. i. For amide functional group tethered product from
solid-phase: (a) Marzinzik, A. L.; Felder, E. R. Tetra-
hedron Lett. 1996, 37, 1003; (b) Shen, D.-M.; Shu, M.;
Chapman, K. T. Org. Lett. 2000, 2, 2789. ii. For hydroxy
functional group tethered product from solid-phase:
Stauffer, S. R.; Katzenellenbogen, J. A. J. Comb. Chem.
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mp: 64°C (enol tautomer), FTIR (KBr): 1595 cm−1 1H
,
NMR (300 MHz, CDCl3): l 15.86 (s, 1H), 7.41–7.38 (m,
1H), 7.35–7.31 (m, 2H), 7.23–7.21 (m, 1H), 2.46 (t, 2H,
J=6.4 Hz), 2.07 (t, 2H, J=6.1 Hz), 1.73 (m, 2H), 1.59
(m, 2H). 13C NMR (75 MHz, CDCl3): l 192.2, 187.9,
137.6, 130.7, 130.1, 128.0, 127.9, 127.3, 108.4, 32.5, 24.8,
23.2, 22.0. Anal. calcd for C13H13ClO2: C, 65.97; H, 5.54;
Cl, 14.98. Found: C, 65.77; H, 5.38; Cl, 14.91.
10. Pashkevich, K. I.; Saloutin, V. I.; Postovskii, I. Ya. Russ.
Chem. Rev. 1981, 50 (2), 180.
11. Furstner, A.; Jumbam, D.; Weidmann, H. Tetrahedron
Lett. 1991, 32, 6695.