Water → HCID 67520597, compound

HRID 1786990Notes

Reaction equation

HRID 1786990 reaction equation
[C:1]([O:9][CH2:10][CH2:11][C:12]([OH:17])([CH3:16])[CH2:13][CH2:14]O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[C:1]([O:9][CH2:10][CH2:11][C:12]([OH:17])([CH3:16])[CH2:13][CH2:14][Br:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67520822HCID 67520822, compound

Product 1

HCID 67520597HCID 67520597, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3,5-dihydroxy-3-methylpentyl benzoate (1.0 g) and carbon tetrabromide (2.78 g) in tetrahydrofuran (30 mL) was added dropwise a solution of triphenylphosphine (2.20 g) in tetrahydrofuran (10 mL) under ice-cooling. After stirring at room temperature for 3 days, water was added, and the mixture was extracted with ethyl acetate. The organic layer washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure, and the residue was separated and purified by silica gel column chromatography (eluent, hexane:ethyl acetate=9:1→6:4) to give the title compound (979 mg) as a colorless oil.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was separated
  7. custompurified by silica gel column chromatography (eluent, hexane:ethyl acetate=9:1→6:4)

Sources & evidence

ORD record
ord-8edad025422d40d3969bed25859bb17d
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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