Aluminium lithium hydride → 4-(2,3-Dihydrobenzofuran-7-yl)-4-methyl-2-(trifluoromethyl)pentane-1,2-diol

HRID 2387296Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[C:11]([OH:29])([C:25]([F:28])([F:27])[F:26])[CH2:12][C:13]([C:16]1[C:24]2[O:23][CH2:22][CH2:21][C:20]=2[CH:19]=[CH:18][CH:17]=1)([CH3:15])[CH3:14])C>C1COCC1>[O:23]1[C:24]2[C:16]([C:13]([CH3:15])([CH3:14])[CH2:12][C:11]([C:25]([F:26])([F:27])[F:28])([OH:29])[CH2:10][OH:9])=[CH:17][CH:18]=[CH:19][C:20]=2[CH2:21][CH2:22]1

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of LiAlH4 (4.52 g, 119 mmol) in 230 mL of THF was treated with a solution of 4-(2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester (27.5 g, 79.4 mmol) in 40 mL of THF at 0° C. over 30 minutes. After stirring overnight, the reaction was cooled to 0° C., quenched with 3 mL of water, and treated with 3 mL of 4 M NaOH solution. After 10 minutes, the mixture was treated with additional 18 mL portion of water and the resulting mixture was warmed to room temperature for 4 hours. The mixture was filtered and the filter cake was washed with five 100 mL portions of diethyl ether. The filtrate was concentrated in vacuo to give 24.0 g of 4-(2,3-dihydrobenzofuran-7-yl)-4-methyl-2-trifluoromethylpentane-1,2-diol as an oil (99%).

Workup

customquenched with 3 mL of water
additiontreated with 3 mL of 4 M NaOH solution
waitAfter 10 minutes
additionthe mixture was treated with additional 18 mL portion of water
temperaturethe resulting mixture was warmed to room temperature for 4 hours
filtrationThe mixture was filtered
washthe filter cake was washed with five 100 mL portions of diethyl ether
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-29f2bcb0d3b74666bfa83543a49f961e
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268859B2

Reaction notes

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