Water → HCID 67520597, compound

HRID 1926077Notes

Reaction equation

HRID 1926077 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 was 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 was 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-d5e2c3f9c8a8464ab255daa7621b78f6
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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