Water → 5-Bromo-6-methoxy-2-naphthalenemethanol

HRID 1609127Notes

Reaction equation

HRID 1609127 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([CH:16]=[O:17])=[CH:9]2.O>CO.C1COCC1>[Br:3][C:4]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8]([CH2:16][OH:17])=[CH:9]2

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 185053535-Bromo-6-methoxy-2-naphthaldehyde

Product 1

HCID 189963225-Bromo-6-methoxy-2-naphthalenemethanolYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Step d) Sodium borohydride (4.78 g, 128.3 mmol) was added portionwise in to a cold (0° C.) mixture of 5-bromo-6-methoxy-2-naphthldehyde (34.0 g, 128.3 mmol) in methanol (300 ml) and THF (200 mL). After stirring for 30 minutes the mixture was poured in to water and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography (hexane/EtOAc 2/1) gave a yellow solid (30.5 g, 90% yield, m.p. 85°-87° C.).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic extracts were dried over MgSO4
  3. customEvaporation and purification by flash chromatography (hexane/EtOAc 2/1)

Sources & evidence

ORD record
ord-ba4027a65eb44e40b3d223c6ae1b2ab5
Source dataset
uspto-grants-1995_03
Patent number
US05399588

Reaction notes

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