Sodium Chloride → Docosa-1,3,5,7,9,11-hexaen-1-ol

HRID 1582725Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7](OCC)(=[O:29])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=[CH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C(OCC)(=O)C.[Cl-].[Na+]>C(OCC)C>[CH:7]([OH:29])=[CH:8][CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=[CH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

Conditions

Temperature: 0 °C

Procedure

1.28 g (33.7 mmol) of lithium aluminum hydride (LiAlH4) and 100 ml of anhydrous dietylether were placed into an eggplant-shape flask of which air had been replaced by argon gas, and kept at 0° C. To the mixture was added dropwise over about 30 minutes the solution of 10 g (28.1 mmol) of ethyl docosahexaenate in diethylether (20 ml of anhydrous diethylether), and then stirred at 0° C. for 30 minutes. After stirring, ethyl acetate and the saturated solution of sodium chloride were added to the reaction mixture, followed by removal of the precipitate by filtration. The filtrate was concentrated under reduced pressure, and purified by silica gel open column chromatography (hexane:ethyl acetate=5:1), to give 5.67 g of docosahexaenol (abbreviated as DHA-OH somewhere hereinafter).

Workup

customkept at 0° C
stirringAfter stirring
customfollowed by removal of the precipitate by filtration
concentrationThe filtrate was concentrated under reduced pressure
custompurified by silica gel open column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record: ord-692427a79787463f8414e5128c8703f0
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06737460B2

Reaction notes

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