Borane → 4-(Hexadecyloxy)-3-(phenylmethoxy)-1-butanol

HRID 255965노트

반응식

HRID 255965 반응식
[CH2:1]([O:17][CH2:18][CH:19]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:20]=[CH2:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].B.[O:31]1CCCC1>>[CH2:1]([O:17][CH2:18][CH:19]([O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:20][CH2:21][OH:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

참가 물질

4

반응물 3

HCID 6331Borane2회HCID 8028Tetrahydrofuran2회HCID 53992725({[1-(Hexadecyloxy)but-3-EN-2-YL]oxy}methyl)benzene

생성물 1

HCID 198665354-(Hexadecyloxy)-3-(phenylmethoxy)-1-butanol

실험 절차

To a solution of 11.5 g of [[[1-[(hexadecyloxy)-methyl]-2-propenyl]oxy]methyl]benzene in 50 ml of tetrahydrofuran was added dropwise, at 0° C.,57.12 ml of 1 M borane in tetrahydrofuran. After stirring at room temperature for 3 hours the excess borane was destroyed by the addition of water. The mixture was cooled in an ice bath, 100 ml of 3N sodium hydroxide was added followed by 100 ml of 30% hydrogen peroxide and after 10 minutes the mixture was stirred for 1/2 hour at room temperature and then diluted with ether. The ether layer was separated, washed with brine, then saturated sodium bisulfite, dried over magnesium sulfate and the solvent removed. The residue was purified by HPLC [hexane: ethyl acetate (9:1)] giving 7.8 g of the desired compound as an oil.

후처리

  1. customwas destroyed by the addition of water
  2. temperatureThe mixture was cooled in an ice bath
  3. addition100 ml of 3N sodium hydroxide was added
  4. additiondiluted with ether
  5. customThe ether layer was separated
  6. washwashed with brine
  7. dry with materialsaturated sodium bisulfite, dried over magnesium sulfate
  8. customthe solvent removed
  9. customThe residue was purified by HPLC [hexane: ethyl acetate (9:1)]

출처 및 근거

ORD 기록
ord-faf215870bc84afd89541f411fd89a89
출처 데이터셋
uspto-grants-1987_10
특허 번호
US04699990

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