Borane → HCID 15097580, compound

HRID 1651256Notes

Reaction equation

HRID 1651256 reaction equation
B.[CH3:2][O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([C:22](O)=[O:23])=[C:11]2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)=[CH:6][CH:5]=1>O1CCCC1>[CH3:2][O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([CH2:22][OH:23])=[C:11]2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6331BoraneHCID 15097579HCID 15097579, compound

Product 1

HCID 15097580HCID 15097580, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of borane in tetrahydrofuran (1M; 10 mL) was added to a solution of crude 7-methoxy-1-(3-methoxyphenyl)-2-naphthalenecarboxylic acid (2 g) in tetrahydrofuran (10 mL) at 0°-5° C. and the mixture was stirred at room temperature for 3 hours. After the solvent was evaporated off, the reaction was diluted with 1N sodium hydroxide and extracted with dichloromethane. The organic layer was washed with brine then was dried (MgSO4) and evaporated to give 1.75 g of crude 7-methoxy-1-(3-methoxyphenyl)-2-naphthalenemethanol.

Workup

  1. customAfter the solvent was evaporated off
  2. additionthe reaction was diluted with 1N sodium hydroxide
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with brine
  5. dry with materialthen was dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-53a96754bd564c08a64fbb66fdaff8b3
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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