Acetic Acid → 6-(Benzyloxy)-2-bromo-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 1802129Notes

Reaction equation

HRID 1802129 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[CH:14]([Br:20])[CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCOCC.CO.[BH4-].[Na+].C(O)(=O)C>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]([OH:19])[CH:14]([Br:20])[CH2:13][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 887MethanolHCID 3283Diethyl EtherHCID 4311764Sodium borohydrideHCID 230870836-(Benzyloxy)-2-bromo-3,4-dihydronaphthalen-1(2h)-one

Product 1

HCID 230872486-(Benzyloxy)-2-bromo-1,2,3,4-tetrahydronaphthalen-1-olYield 91.8%

Conditions

Temperature
3.5 °C

Procedure

6-Benzyloxy-2-bromo-3,4-dihydro-2H-naphthalen-1-one (32.9 g, 0.0964 mol) was dissolved in ether (200 mL, 2 mol) and methanol (30.0 mL, 0.740 mol), cooled with ice bath to internal temperature of 3° C. Sodium tetrahydroborate (1.82 g, 0.0482 mol) was added portionwise over 15 min at 3° C.-8° C. (internal). The mixture was stirred at 2-5° C. for 1 hour. Acetic acid (2.74 mL, 0.0482 mol) was added and the mixture was quenched with water, extracted with EtOAc (100 mL), washed with water (2×), brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give a crude intermediate, 6-(benzyloxy)-2-bromo-1,2,3,4-tetrahydronaphthalen-1-ol (29.5 g).

Workup

  1. customthe mixture was quenched with water
  2. extractionextracted with EtOAc (100 mL)
  3. washwashed with water (2×), brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6e2fcf7e5bff436e95a1ae25a84cd1b1
Source dataset
uspto-grants-2013_01
Patent number
US08349849B2

Reaction notes

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