Aluminium lithium hydride → HCID 66891227, compound

HRID 250175Notes

Reaction equation

[O:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:20]2[CH:25]=[CH:24][C:23]([C:26]#[C:27][CH:28]([OH:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[C:22]([CH3:34])[CH:21]=2)([CH2:18][CH3:19])[CH2:16][CH3:17])=[CH:11][C:10]=1[CH3:35])[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[O:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:20]2[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[CH:28]([OH:33])[C:29]([CH3:32])([CH3:31])[CH3:30])=[C:22]([CH3:34])[CH:21]=2)([CH2:16][CH3:17])[CH2:18][CH3:19])=[CH:11][C:10]=1[CH3:35])[Si:2]([C:5]([CH3:6])([CH3:7])[CH3:8])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 1-(4-{1-[4-(tert-butyl-dimethylsiloxy)-3-methylphenyl]-1-ethylpropyl}-2-methylphenyl)-4,4-dimethylpent-1-yn-3-ol (0.22 g, 0.45 mmol) in anhyd THF (2 mL) was added LiAlH4 (19 mg, 0.49 mmol). The reaction mixture was heated at 65° C. for 6 h. After cooling to ambient temperature, the reaction mixture was quenched sequentially with H2O (0.21 mL), 15% NaOH (0.21 mL) and then H2O (0.63 mL). The resulting mixture was diluted with Et2O, filtered through Celite, washed with brine, dried (Na2SO4) and concentrated to yield (E)-1-(4-{1-[4-(tert-butyl-dimethylsiloxy)-3-methylphenyl]-1-ethylpropyl)-2-methylphenyl)-4,4-dimethylpent-1-en-3-ol (0.15 g, 68%), which was used without purification in the next step.

Workup

temperatureAfter cooling to ambient temperature
customthe reaction mixture was quenched sequentially with H2O (0.21 mL), 15% NaOH (0.21 mL)
additionThe resulting mixture was diluted with Et2O
filtrationfiltered through Celite
washwashed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-25042376879d4875b8b478d0bdd1702f
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863298B2

Reaction notes

Loading…