Acetic Anhydride → (R)-3-methyl-1-cyclopentadecenyl acetate

HRID 1454422Notes

Reaction equation

C1(C)C=CC=CC=1.C[Zn]C.[C:11]([O:14][C:15](=[O:17])[CH3:16])(=O)[CH3:12].[C:18]1(=O)[CH2:32][CH2:31]C[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH:20]=[CH:19]1>C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Cu+2].C1(C)C=CC=CC=1>[C:15]([O:14][C:11]1[CH2:31][CH2:32][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C@@H:28]([CH3:29])[CH:12]=1)(=[O:17])[CH3:16]

Participants

Conditions

Temperature: -20 °C

Procedure

Under a nitrogen atmosphere 55 mg (0.121 mmol) of an optically active ligand 4-(cis-2,6-dimethylpiperidine)-(R)-ditetrahydronaphthodioxaphosphepin, 14.5 mg (0.04 mmol) of Cu(OTf)2, 2.55 ml (4.8 mmol) of a dimethylzinc toluene solution (1.88 mol/L), and 5 ml of toluene were added to a 30-ml reaction flask and cooled to −20° C. Then, a mixed solution containing 410 mg (4 mmol) of acetic anhydride, 889 mg (4 mmol) of (2E)-cyclopentadecenone and 5 ml of toluene was added thereto dropwise over 5 minutes, and the resultant mixture was stirred additionally for 4 hours until completion of the reaction was determined by gas chromatographic analysis. The reaction was terminated by addition of an aqueous 5% sulfuric acid solution after completion of the reaction to give 1.2 g of crude (R)-3-methyl-1-cyclopentadecenyl acetate.

Workup

additionwas added
customThe reaction was terminated by addition of an aqueous 5% sulfuric acid solution
customafter completion of the reaction

Sources & evidence

ORD record: ord-913aa1d18d3c41da82ee374ba2be55cf
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07479574B2

Reaction notes

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