Carbon Tetrachloride → HCID 29271082, compound

HRID 1510116Notes

Reaction equation

HRID 1510116 reaction equation
[CH3:1][C@@H:2]([O:5][C:6]1[CH:7]=[C:8]([CH2:12]O)[CH:9]=[CH:10][CH:11]=1)[CH2:3][CH3:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:34]>>[Cl:34][CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([O:5][C@H:2]([CH3:1])[CH2:3][CH3:4])[CH:7]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 28065545HCID 28065545, compound

Product 1

HCID 29271082HCID 29271082, compound

Procedure

To a solution of (3-{[(1R)-1-methylpropyl]oxy}phenyl)methanol (1.01 g, 5.60 mmol) in carbon tetrachloride (18.7 ml) was added triphenylphosphine (1.40 g, 5.32 mmol). The reaction was heated to reflux overnight. The reaction was filtered through a fritted funnel and washed with carbon tetrachloride. The filtrate was concentrated. The residue was purified on a silica gel cartridge (0% EtOAc/hexanes to 10% EtOAc/hexanes) to give the desired product.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. filtrationThe reaction was filtered through a fritted funnel
  4. washwashed with carbon tetrachloride
  5. concentrationThe filtrate was concentrated
  6. customThe residue was purified on a silica gel cartridge (0% EtOAc/hexanes to 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-fdf27cecc6d74785a564953d7af17632
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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