Benzyl Bromide → HCID 21882780, compound

HRID 722134Notes

Reaction equation

HRID 722134 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:12][CH:11]3[C:13](=[O:14])[CH:8]([CH2:9][CH2:10]3)[CH2:7][C:6]=2[CH:15]=1.C([O-])([O-])=O.[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.O>[CH2:22]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:12][CH:11]3[C:13](=[O:14])[CH:8]([CH2:9][CH2:10]3)[CH2:7][C:6]=2[CH:15]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 130264432-Hydroxy-5,6,7,8,9,10-hexahydro-6,9-methanobenzo[8]annulen-11-one

Product 1

HCID 21882780HCID 21882780, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-hydroxy-5,6,7,8,9,10-hexahydro-6,9-methanobenzo[a][8]annulen-11-one (15 g; J. Org. Chem 1982, 47, 4329), K2CO3 (20.5 g) and benzyl bromide (10.6 ml) in DMF (100 ml) was stirred for 48 hrs at room temperature. The reaction was diluted with water (500 ml) and extracted with EtOAc (3×150 ml). The combined organic phases were washed with water (2×300 ml), brine (150 ml), dried and concentrated to give a gummy oil which crystallized on standing and after trituration with ether the title benzyl ether (19.5 g, 90%) as a white solid (360 MHz 1H, δ-CDCl3) 1.32 (2H, m), 1.85 (2H, m), 2.57 (2H, m), 2.87 (4H, m), 5.05 (2H, s), 6.82 (2H, m), 7.11 (1H, d, J=8.2), 7.37 (5H, m).

Workup

  1. extractionextracted with EtOAc (3×150 ml)
  2. washThe combined organic phases were washed with water (2×300 ml), brine (150 ml)
  3. customdried
  4. concentrationconcentrated
  5. customto give a gummy oil which
  6. customcrystallized

Sources & evidence

ORD record
ord-07c2066eed674bf0bc9fb2ddf0f66602
Source dataset
uspto-grants-2006_11
Patent number
US07138400B2

Reaction notes

Loading…