Water → Ethyl 8-carbamoyl-12-hydroxy-12-methylheptadecanoate

HRID 973352노트

반응식

HRID 973352 반응식
[C:1]([CH:4]([CH2:16][CH2:17][CH:18]=[C:19]([CH3:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:3])[NH2:2].[BH4-].[Na+].[OH2:28]>O1CCCC1.[OH-].[Na+]>[C:1]([CH:4]([CH2:16][CH2:17][CH2:18][C:19]([OH:28])([CH3:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:3])[NH2:2]

참가 물질

6

반응물 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 54022520Ethyl 8-carbamoyl-12-methyl-11-heptadecenoate

생성물 1

HCID 21401727Ethyl 8-carbamoyl-12-hydroxy-12-methylheptadecanoate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 14798Sodium Hydroxide용매2회

실험 절차

Mercuric acetate (3.8 g., 0.012 mole) is dissolved in water (12 ml.) and tetrahydrofuran (20 ml.) is added to give a suspension of a yellow solid. Then, ethyl 8-carbamoyl-12-methyl-11-heptadecenoate (4.2 g., 0.012 mole) in tetrahydrofuran (20 ml.) is added, and the mixture stirred at room temperature for 24 hours. After 6 hours, the yellow suspended solid has disappeared and a cloudy solution results. To the solution is added 3M sodium hydroxide solution (12 ml.), followed by 0.5M sodium borohydride solution in 3M sodium hydroxide (12 ml.). Liquids are decanted from the precipitated mercury. The organic layer is taken up in ether, washed with three portions of water and dried over sodium sulfate. Evaporation of the ether leaves 4.0 g. of ethyl 8-carbamoyl-12-hydroxy-12-methylheptadecanoate which is used in the next step without further purification.

후처리

  1. customto give
  2. additiona suspension of a yellow solid
  3. waitAfter 6 hours
  4. customa cloudy solution results
  5. customLiquids are decanted from the precipitated mercury
  6. washwashed with three portions of water
  7. dry with materialdried over sodium sulfate
  8. customEvaporation of the ether
  9. customleaves 4.0 g
  10. customof ethyl 8-carbamoyl-12-hydroxy-12-methylheptadecanoate which is used in the next step without further purification

출처 및 근거

ORD 기록
ord-4c48f6c845524826a2bfa2016191cb3b
출처 데이터셋
uspto-grants-1977_10
특허 번호
US04055597

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