Nonane → HCID 14261110, compound

HRID 1085661Notes

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.CCCCCCCCC>>[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 8141Nonane

HCID 84564Bis(trimethylsilyl)acetylene

HCID 2757989Cyclohexylacetyl chloride

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

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-borabiccyclo[3.3.1]nonane ((S)-Alpine-BoraneR, 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-31af14aec6cd4bfd8052255589f6c08a
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05010189

Reaction notes

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