Hydrochloric Acid → Methyl 2-hydroxy-4-[3-hydroxy-3-(8,8-dimethyl-5,6,7,8-tetrahydro-2-naphthyl)-1-propynyl]benzoate

HRID 428220Notes

Reaction equation

HRID 428220 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([C:12]#[C:13][C:14](=[O:27])[C:15]2[CH:24]=[CH:23][C:22]3[CH2:21][CH2:20][CH2:19][C:18]([CH3:26])([CH3:25])[C:17]=3[CH:16]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C1COCC1.[BH4-].[Na+].Cl>CO>[OH:1][C:2]1[CH:11]=[C:10]([C:12]#[C:13][CH:14]([OH:27])[C:15]2[CH:24]=[CH:23][C:22]3[CH2:21][CH2:20][CH2:19][C:18]([CH3:25])([CH3:26])[C:17]=3[CH:16]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 18357927HCID 18357927, compound

Product 1

HCID 18357928Methyl 2-hydroxy-4-[3-hydroxy-3-(8,8-dimethyl-5,6,7,8-tetrahydro-2-naphthyl)-1-propynyl]benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7.95 g (22 mol) of methyl 2-hydroxy-4-[3-oxo-3-(8,8-dimethyl-5,6,7,8-tetrahydro-2-naphthyl)-1-propynyl]benzoate, 150 ml of THF and 20 ml of methanol are introduced into a round-bottomed flask. 660 mg (17.4 mmol) of sodium borohydride are added portionwise and the mixture is stirred at room temperature for two hours. The reaction medium is poured into ice-water, neutralized with hydrochloric acid and extracted with ethyl acetate, and the organic phase is separated out after settling has taken place, washed with water, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (80/20). After evaporation of the solvents, 3.8 g (47.5%) of the expected product are collected in the form of an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase is separated out after settling
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a column of silica
  8. washeluted with a mixture of heptane and ethyl acetate (80/20)
  9. customAfter evaporation of the solvents, 3.8 g (47.5%) of the expected product
  10. customare collected in the form of an oil

Sources & evidence

ORD record
ord-05d3c0a617f54180afdb1c363364dcd6
Source dataset
uspto-grants-2001_11
Patent number
US06313162B1

Reaction notes

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