Aluminium lithium hydride → HCID 25010673, compound

HRID 1925670Notes

Reaction equation

[CH3:1]/[C:2](/[CH2:9][CH2:10][CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH3:27])=[CH:3]\[C:4](OCC)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1]/[C:2](/[CH2:9][CH2:10][CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20]/[CH:21]=[CH:22]\[CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH3:27])=[CH:3]\[CH2:4][OH:5]

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl (2E,7Z,10Z,13Z,16Z,19Z)-3-methyl-docosa-2,7,10,13,16,19-hexaenoate (2E:2Z=9:1), (0.40 g, 1.08 mmol) was dissolved in dry THF (5 mL) and added dropwise to a cold suspension of LAH (0.045 g, 1.19 mmol) in dry THF (10 mL). The mixture was stirred at 0° C. under inert atmosphere for 30 minutes, followed by 18 hours at ambient temperature. The reaction was quenched by addition of 10% NH4Cl (20 mL) and the mixture was extracted twice with heptane (30 mL). The combined organic extracts were washed with brine (20 mL) and dried (Na2SO4). Purification by flash chromatography (heptane:EtOAc 4:1) afforded 0.16 g (45%) of 3-methyl-(2E,7Z,10Z,13Z,16Z,19Z)-docosa-2,7,10,13,16,19-hexaen-1-ol as a colourless oil.

Workup

waitfollowed by 18 hours at ambient temperature
customThe reaction was quenched by addition of 10% NH4Cl (20 mL)
extractionthe mixture was extracted twice with heptane (30 mL)
washThe combined organic extracts were washed with brine (20 mL)
dry with materialdried (Na2SO4)
customPurification by flash chromatography (heptane:EtOAc 4:1)

Sources & evidence

ORD record: ord-50f590ccf80f4397ad9db8436d3e7e4b
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178708B2

Reaction notes

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