Boron tribromide → 5,6,7,8-Tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl ethyl ketone

HRID 1883274Notes

Reaction equation

HRID 1883274 reaction equation
C[O:2][C:3]1[C:4]([C:17](=[O:20])[CH2:18][CH3:19])=[CH:5][C:6]2[C:7]([CH3:16])([CH3:15])[CH2:8][CH2:9][C:10]([CH3:14])([CH3:13])[C:11]=2[CH:12]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[C:4]([C:17](=[O:20])[CH2:18][CH3:19])=[CH:5][C:6]2[C:7]([CH3:15])([CH3:16])[CH2:8][CH2:9][C:10]([CH3:13])([CH3:14])[C:11]=2[CH:12]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 235108141-(3-Methoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-propan-1-one2×

Product 1

HCID 235108275,6,7,8-Tetrahydro-3-hydroxy-5,5,8,8-tetramethyl-2-naphthyl ethyl ketoneYield 126.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3-methoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-propan-1-one (Intermediate 12, 2.07 g, 7.9 mmol) in CH2Cl2 (40 mL) at 0° C. was added BBr3 (8.9 mL, 1M in CH2Cl2 8.9 mmol) dropwise. After 30 min, the reaction was quenched with ice-H2O, and extracted with EtOAc. The organic layer was washed with brine, dried-over Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (2% EtOAc-hexane) to give the title compound as a white solid (2.6 g, 90%).

Workup

  1. customthe reaction was quenched with ice-H2O
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine, dried-over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel (2% EtOAc-hexane)

Sources & evidence

ORD record
ord-395829a171fd47818c28f8b00d62c898
Source dataset
uspto-grants-2004_07
Patent number
US06759547B1

Reaction notes

Loading…