Methoxymethyl-triphenylphosphonium chloride → HCID 76594468, compound

HRID 1867647Notes

Reaction equation

HRID 1867647 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:6][O:7][CH2:8][C:9]1([CH:19]=[CH2:20])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)C(O)[O:10]1.[Cl-].[CH3:31][O:32][CH2:33][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:53]C(C)([O-])C.[K+]>O1CCCC1>[F:1][C:2]([F:28])([F:29])[C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([C:24]([F:26])([F:25])[F:27])[CH:23]=1)[CH2:6][O:7][CH2:8][C:9]([C:17]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH:53]=[CH:33][O:32][CH3:31])([OH:10])[CH:19]=[CH2:20]

Participants

5

Reactant 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 57691458HCID 57691458, compound

Product 1

HCID 76594468HCID 76594468, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-3-vinyl-1,3-dihydroisobenzofuran-1-ol (475 mg, 1.14 mmol) and (methoxymethyl)triphenylphosphonium chloride (973 mg, 2.84 mmol) in tetrahydrofuran (6 mL) at 0° C. was added potassium tert-butoxide (319 mg, 2.84 mmol). The ice bath was removed and stirring continued for 6 h. The reaction was quenched by addition of saturated ammonium chloride and poured into diethyl ether. The ethereal was washed with water, then brine, dried over magnesium sulfate, and concentrated. Column chromatography (12%-->25% EtOAc/Hex) gave 210 mg (41%) as a colorless oil. Mass spec.: 469.23 (MNa)+.

Workup

  1. customThe ice bath was removed
  2. customThe reaction was quenched by addition of saturated ammonium chloride
  3. additionpoured into diethyl ether
  4. washThe ethereal was washed with water
  5. dry with materialbrine, dried over magnesium sulfate
  6. concentrationconcentrated
  7. customColumn chromatography (12%-->25% EtOAc/Hex) gave 210 mg (41%) as a colorless oil

Sources & evidence

ORD record
ord-03d768603ce34d778f2556395b3dab76
Source dataset
uspto-grants-2009_12
Patent number
US07632861B2

Reaction notes

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