Sodium borohydride → HCID 10902156, 화합물

HRID 582902노트

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HRID 582902 반응식
[O:1]1[C@H:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:2]1[C:3](OC)=[O:4].[BH4-].[Na+]>O1CCCC1>[O:1]1[C@H:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C@H:2]1[CH2:3][OH:4]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 56999066HCID 56999066, 화합물

생성물 1

HCID 10902156HCID 10902156, 화합물수율 75%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

In 500 ml of tetrahydrofuran were suspended 62.4 g (0.2 mol) of the methyl (2S,3R)-2,3-epoxyoctadecanoate (V-1) prepared in Example 3-(3) and 7.4 g (0.2 mol) of NaBH4, followed by heat refluxing for 3 hours. After confirming disappearance of the compound (V-1) by TLC, tetrahydrofuran was evaporated. To the residue were added 20 ml of water and then 500 ml of a saturated ammonium chloride aqueous solution to adjust to pH 5 to 6, and the mixture was extracted with 500 ml of ethyl acetate. After drying, ethyl acetate was removed by evaporation, and the resulting crude crystals were recrystallized from heptane to obtain 42.6 g (0.15 mol; yield: 75%) of (2R,3R)-2,3-epoxyoctadecanol (melting point: 77 to 78° C.). Optical rotation [α]D25 =+24.5° (c=0.285, CHCl3)

후처리

  1. temperatureby heat
  2. temperaturerefluxing for 3 hours
  3. customwas evaporated
  4. additionTo the residue were added 20 ml of water
  5. extractionthe mixture was extracted with 500 ml of ethyl acetate
  6. customAfter drying
  7. customethyl acetate was removed by evaporation
  8. customthe resulting crude crystals were recrystallized from heptane

출처 및 근거

ORD 기록
ord-0b1b40ca4bb641a3a0d2421a717da038
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05925792

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