Diisobutylaluminumhydride → HCID 19375044, compound
Reaction equation
C([O:3][C:4](=O)/[C:5](/[CH3:18])=[CH:6]/[CH2:7][CH2:8][C:9]1[C:14]([CH3:16])([CH3:15])[CH2:13][CH2:12][CH2:11][C:10]=1[CH3:17])C.[H-].C([Al+]CC(C)C)C(C)C>>[CH3:18]/[C:5](=[CH:6]\[CH2:7][CH2:8][C:9]1[C:14]([CH3:16])([CH3:15])[CH2:13][CH2:12][CH2:11][C:10]=1[CH3:17])/[CH2:4][OH:3]Participants
Procedure
2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde is reacted with methoxymethyl triphenylphosphonium chloride in the presence of potassium tert-butoxide, followed by conversion to the dimethyl acetal and subsequent hydrolysis, as described in Example 1 above, to provide 3-(2,6,6-trimethyl-1-cyclohexen-1yl)propanal (80% yield) as a colorless oil after distillation in vacuo. This material (6.8 g) is reacted with triethyl 2-phosphonopropionate (10.6 ml) by the method of example 14(B) above, to provide 6.58 g (2E)-2-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-pentenoic acid ethyl ester as a colorless oil after chromatography. This ester is reduced with diisobutylaluminum hydride by the method described in example 14(B) above, to provide (2E)-2-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-pentenol as a colorless oil (93%) after chromatography.
Sources & evidence
- ORD record
- ord-9a72512fe11f4a2f8f703d6d6c612bc5
- Source dataset
- uspto-grants-1995_11
- Patent number
- US05464865
Reaction notes
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