Bis(trimethylsilyl)acetylene → HCID 14261110, compound

HRID 1199264Notes

Reaction equation

C[Si](C#C[Si](C)(C)C)(C)C.C1(CC(Cl)=O)CCCCC1.[CH:21]1([CH2:27][C:28](=[O:31])[C:29]#[CH:30])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[C@@H]12CC(C1(C)C)CC(B1C3CCCC1CCC3)C2C>>[CH:21]1([CH2:27][C@H:28]([OH:31])[C:29]#[CH:30])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

Reactant 4

HCID 84564Bis(trimethylsilyl)acetylene

HCID 2757989Cyclohexylacetyl chloride

HCID 142611081-Cyclohexyl-3-butyn-2-one

HCID 67416678HCID 67416678, compound

Product 1

HCID 14261110HCID 14261110, compound

Procedure

As directed by D. R. M. Walton and F. Waugh, J. Organomet. Chem. 37, 45 (1972), bis(trimethylsilyl)acetylene is acylated with cyclohexylacetic acid chloride and hydrolysed with aqueous/methanolic borax solution to 1-cyclohexyl-3-butyn-2-one. Reduction with (S)-B-(3-pinanyl)-9-borabicyclo[3.3.1]nonane ((S)-Alpine-Borane®, Aldrich, 88% ee) as directed by M. M Midland et al., Tetrahedron 40, 1371 (1984) yields 1-cyclohexyl-3-butyn-2(S)-ol.

Sources & evidence

ORD record: ord-ac2f05701fc6453b8e6d84bf1668439a
Source dataset: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04898977

Reaction notes

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