Sodium borohydride → 1-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2-(4-carboxyphenoxy)ethanol

HRID 653834Notes

Reaction equation

HRID 653834 reaction equation
[CH3:1][C:2]1([CH3:29])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](=[O:28])[CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([O:25]CC)=[O:24])=[CH:19][CH:18]=3)[CH:5]=[CH:4][C:3]1=2.[BH4-].[Na+]>O1CCCC1.CO.[Cl-].[Na+].O>[CH3:1][C:2]1([CH3:29])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([CH:14]([OH:28])[CH2:15][O:16][C:17]3[CH:18]=[CH:19][C:20]([C:23]([OH:25])=[O:24])=[CH:21][CH:22]=3)[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 19890287HCID 19890287, compound

Product 1

HCID 147957241-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2-(4-carboxyphenoxy)ethanolYield 76%

Reagents, catalysts & solvents 2

HCID 21899815MeOH tetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2.1 g (5 mmol) of 1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-2-(4-ethoxycarbonylphenoxy)ethanone (from Example 5) in 100 ml of tetrahydrofuran/methanol (2:1) were stirred with 0.4 g (10 mmol) of sodium borohydride at room temperature for 30 min; the reaction solution was poured into saturated brine and extracted with ethyl acetate; the extracts were washed with water, dried over magnesium sulfate and evaporated to provide an oily residue which was subjected to alkaline hydrolysis as described in Example 6 and yielded after appropriate working up 1.4 g of the title compound; melting point (cyclohexane): 160°-162° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto provide an oily residue which
  6. customhydrolysis
  7. customyielded

Sources & evidence

ORD record
ord-61fe0fdf166d4a828b516f3f15f35e78
Source dataset
uspto-grants-1992_07
Patent number
US05128479

Reaction notes

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