Ethanol → 2-Hexyl-3-hydroxy-5-[(tetrahydro-2H-pyran-2-yl)oxy]-hexadecanoic Acid Methyl Ester

HRID 703680노트

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HRID 703680 반응식
[CH2:1]([CH:7]([C:12](=[O:33])[CH2:13][CH:14]([O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:8]([O:10][CH3:11])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C(O)C.[BH4-].[Na+]>C1COCC1>[CH2:1]([CH:7]([CH:12]([OH:33])[CH2:13][CH:14]([O:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][O:28]1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:8]([O:10][CH3:11])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

참가 물질

5

반응물 3

HCID 702EthanolHCID 4311764Sodium borohydride2회HCID 217639352-Hexyl-3-oxo-5-[(tetrahydro-2H-pyran-2-yl)oxy]-hexadecanoic Acid Methyl Ester(Mixture of Diastereomers)

생성물 1

HCID 197947662-Hexyl-3-hydroxy-5-[(tetrahydro-2H-pyran-2-yl)oxy]-hexadecanoic Acid Methyl Ester수율 98.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-5 °C

실험 절차

7.76 g of methyl 2-hexyl-3-oxo -5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoate are dissolved in 500 ml of THF while gassing with argon, treated with 20 ml of ethanol and cooled to -5° C. 5.3 g of NaBH4 are added portionwise while stirring in such a manner that the temperature does not exceed 0° C. After stirring for 3 hours the excess sodium borohydride is filtered off, the reaction mixture is hydrolyzed (to pH 6) with 2N hydrochloric acid in the cold and the solvent is evaporated off. The residue is extracted with ether and the ethereal phase is dried and evaporated. There are obtained 7.71 g of methyl 2-hexyl-3-hydroxy-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoate.

후처리

  1. customdoes not exceed 0° C
  2. filtrationis filtered off
  3. customis evaporated off
  4. extractionThe residue is extracted with ether
  5. customthe ethereal phase is dried
  6. customevaporated

출처 및 근거

ORD 기록
ord-9b1362187e6049298c9761e7e9eefc5f
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04983746

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