Water → HCID 59488774, compound

HRID 221946Notes

Reaction equation

HRID 221946 reaction equation
[Br:1][C:2]1[C:3]([C:21](OC)=[O:22])=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH3:20])=[CH:15][CH:14]=1)[CH:8]=[CH:7][CH:6]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C(OCC)C>[Br:1][C:2]1[C:3]([CH2:21][OH:22])=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH3:20])=[CH:17][CH:18]=1)[CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 59488764HCID 59488764, compound

Product 1

HCID 59488774HCID 59488774, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under a nitrogen stream, methyl 3-bromo-5-[(4-ethylphenyl)methyl]-2-naphthoate (334.1 mg, 0.87 mmol) was dissolved in diethyl ether (10.0 mL). To the resultant mixture was added lithium aluminum hydride (39.7 mg, 1.04 mmol) under ice-cooling, and the resultant mixture was stirred for 30 minutes. Water was added thereto, and the resultant mixture was extracted with dichloromethane. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure, to thereby obtain the titled compound (305.8 mg, 89%).

Workup

  1. temperaturecooling
  2. extractionthe resultant mixture was extracted with dichloromethane
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fa4f5774a1e14f129014154fb24bee42
Source dataset
uspto-grants-2012_06
Patent number
US08207134B2

Reaction notes

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