Potassium tert-butoxide → HCID 59227503, compound

HRID 1640053Notes

Reaction equation

HRID 1640053 reaction equation
[C:1]1([C:7]#[C:8][CH2:9][O:10][SiH:11]([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.CC([O-])(C)C.[K+]>>[C:1]1([C:7]2[Si:11]([CH:15]([CH3:17])[CH3:16])([CH:12]([CH3:13])[CH3:14])[O:10][CH2:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

3

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 59227494HCID 59227494, compound

Product 1

HCID 59227503HCID 59227503, compound

Procedure

Using (3-cyclohexenylprop-2-ynyloxy)diisopropylsilane (0.715 g, 2.854 mmol) and KOtBu (0.037 g, 0.330 mmol) produced a crude product as a colorless, clear liquid which upon flash chromatography yielded the title compound as clear colorless liquid; Rf 0.45 (hexanes/Et2O, 15:2). The isolated compound was found to have an impurity of about ˜20% with a close Rf value, hence the compound was further purified by using a chromatotron (2.0 mm silica gel) (0.537 g, 2.144 mmol, 75.1%). 1H NMR (300 MHz, CDCl3) δ 6.56 (s, 1H, H-4), 5.57 (s, 1H, H-9), 4.61 (s, 1H, H-5), 2.17-2.26 (m, 2H, H-13), 2.03-2.16 (m, 2H, H-10), 1.64-1.75 (m, 2H, H-12), 1.52-1.64 (m, 2H, H-11), 1.06-1.20 (m, 2H, H-6), 1.04 (d, J=6.6 Hz, 6H, H-7), 0.98 (d, J=6.8 Hz, 6H, H-7); 13C NMR (300 MHz, CDCl3) δ 140.3 (C-3), 138.0 (C-4), 135.7 (C-8), 128.9 (C-9), 77.8 (C-5), 26.2 (C-13), 26.0 (C-10), 22.8 (C-12), 22.4 (C-11), 17.4 (C-7), 17.1 (C-7), 13.4 (C-6); HRMS calcd for C15H27OSi (M+H)+ 251.1831. found 251.1828.

Workup

  1. customproduced a crude product as a colorless, clear liquid which upon flash chromatography

Sources & evidence

ORD record
ord-e88d745b54d64570b260cdd52e69bb82
Source dataset
uspto-grants-2012_02
Patent number
US08110695B2

Reaction notes

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