Trimethylsilylacetylene → HCID 69592544, compound

HRID 1829633Notes

Reaction equation

[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].[Li]CCCC.[Si:12]([O:29][C@@H:30]1[CH2:47][CH2:46][C@@:45]2([CH3:48])[C@@H:32]([CH2:33][CH2:34][C@@H:35]3[C@@H:44]2[CH2:43][CH2:42][C@@:40]2([CH3:41])[C@H:36]3[CH2:37][CH2:38][C@@H:39]2[CH:49]=[O:50])[CH2:31]1)([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[CH3:1][Si:2]([CH3:4])([CH3:3])[C:5]#[C:6][CH:49]([C@H:39]1[CH2:38][CH2:37][C@H:36]2[C@H:35]3[C@H:44]([CH2:43][CH2:42][C@:40]12[CH3:41])[C@:45]1([CH3:48])[C@H:32]([CH2:31][C@H:30]([O:29][Si:12]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:47][CH2:46]1)[CH2:33][CH2:34]3)[OH:50]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of trimethylsilylacetylene (0.24 mL, 1.715 mmol) in anhydrous THF (5.7 mL) at 0° C. was added a solution of n-BuLi (1.07 mL, 1.715 mmol) 1.6 M in hexanes and the resulting mixture was stirred for 2 h. Subsequently, the mixture was cooled to −78° C. and a solution of 3α-(t-butyidiphenylsilyloxy)-5α-androstan-17β-carboxaldehyde (310 mg, 0.57 mmol) in THF (5.7 mL) was added and the mixture was stirred at this temperature for 3 h. Quenching of the reaction by the addition of NH4Cl was followed by extraction with ethyl acetate.

Workup

stirringthe mixture was stirred at this temperature for 3 h
customQuenching of the reaction by the addition of NH4Cl
extractionwas followed by extraction with ethyl acetate

Sources & evidence

ORD record: ord-267a69c4a43c4c188de49d3afb044cb7
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07064116B2

Reaction notes

Loading…