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

HRID 973352Notes

Reaction equation

HRID 973352 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 14798Sodium HydroxideSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4c48f6c845524826a2bfa2016191cb3b
Source dataset
uspto-grants-1977_10
Patent number
US04055597

Reaction notes

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