HCID 54208735, compound → HCID 54456306, compound

HRID 1732252Notes

Reaction equation

HRID 1732252 reaction equation
C(OCC(C)CCCC(C)=CCCC(=O)C[Br:20])C1C=CC=CC=1.[O:24]([CH2:42][CH:43]([CH3:59])[CH2:44][CH2:45][CH2:46][C:47]([CH3:58])=[CH:48][CH2:49][CH2:50][C:51]([O:53][Si](C)(C)C)=[CH2:52])[Si:25]([C:38]([CH3:41])([CH3:40])[CH3:39])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[O:24]([CH2:42][CH:43]([CH3:59])[CH2:44][CH2:45][CH2:46][C:47]([CH3:58])=[CH:48][CH2:49][CH2:50][C:51](=[O:52])[CH2:53][Br:20])[Si:25]([C:38]([CH3:41])([CH3:40])[CH3:39])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 54208735HCID 54208735, compoundHCID 54218865HCID 54218865, compound

Product 1

HCID 54456306HCID 54456306, compound

Procedure

Following the procedure for the preparation of 11-benzyloxy-1-bromo-6,10-dimethyl-2-oxo-undec-5-ene, but employing 11-t-butyldiphenylsiloxy-6,10-dimethyl-2-trimethylsiloxy-undec-1,5-diene (44.5 g) in place of 11-benzyloxy-6,10-dimethyl-2-trimethylsiloxy-undec-1,5-diene, 11-t-butyldiphenylsiloxy-1-bromo-6,10-dimethyl-2-oxo-undec-5-ene (45.8 g) is obtained as a yellow oil. Chromatography of a portion of the oil on silica using ethyl acetate-hexane gradients gives the pure product:

Sources & evidence

ORD record
ord-4b5ff4effcd24a8ebb50918b51ca9515
Source dataset
uspto-grants-1980_12
Patent number
US04237055

Reaction notes

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