Methoxymethyl-triphenylphosphonium chloride → HCID 22631197, compound
Reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Na+].[Cl-].[CH3:12][O:13][CH2:14][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[N:34]1[CH:39]=[CH:38][N:37]=[CH:36][C:35]=1[C:40]1[CH:47]=[CH:46][C:43]([CH:44]=O)=[CH:42][CH:41]=1>C1COCC1>[CH3:12][O:13]/[CH:14]=[CH:44]/[C:43]1[CH:46]=[CH:47][C:40]([C:35]2[CH:36]=[N:37][CH:38]=[CH:39][N:34]=2)=[CH:41][CH:42]=1Participants
5
Conditions
- Temperature
- -10 °C
Procedure
Sodium hexamethyldisilazide (10.80 mL, 10.80 mmol, 1.0M in THF) was added to a suspension of methoxymethyltriphenylphosphonium chloride (3.72 g, 10.80 mmol) in THF (20 mL) at −10° C., and the red-orange mixture was stirred for 15 min at −10° C. A solution of 4-pyrazinylbenzaldehyde (1.00 g, 5.43 mmol) prepared as described in reference example 17) in THF (3 mL) was added dropwise, and stirring was continued at −10° C. for 1 h. The reaction mixture was quenched with sat. aq. NH4Cl, extracted with ethyl acetate, the organic layer dried with Na2SO4, and concentrated in vacuo. Purification by medium pressure liquid chromatography (SiO2, 3:1 hexane/ethyl acetate) yielded 820 mg (71%) of the title compound (E:Z=1:1). MS 213 (M+H)+.
Workup
- additionwas added dropwise
- stirringstirring
- waitwas continued at −10° C. for 1 h
- customThe reaction mixture was quenched with sat. aq. NH4Cl
- extractionextracted with ethyl acetate
- dry with materialthe organic layer dried with Na2SO4
- concentrationconcentrated in vacuo
- customPurification by medium pressure liquid chromatography (SiO2, 3:1 hexane/ethyl acetate)
Sources & evidence
- ORD record
- ord-af84369cb0384efdb53e3d65986138ef
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06825170B2
Reaction notes
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