Benzyl Alcohol → HCID 57459601, compound
Reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:11][C:12]1[C:17]([C:18]([F:21])([F:20])[F:19])=[C:16](Cl)[CH:15]=[CH:14][N:13]=1>CN(C=O)C>[CH2:3]([O:10][C:16]1[CH:15]=[CH:14][N:13]=[C:12]([Cl:11])[C:17]=1[C:18]([F:20])([F:21])[F:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of NaH (0.487 g, 12.732 mmol, 60% mineral oil) in DMF (50 ml) cooled at 0° C., was added benzyl alcohol (1.262 ml, 12.2 mmol). The resulting mixture was stirred for 2 min. Then, intermediate compound D6 (2.5 g, 11.575 mmol) was added. The resulting reaction mixture was gradually warmed to room temperature and stirred for 1 h. The reaction mixture was quenched with water and extracted with Et2O. The organic layer was separated, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography (silica gel; Heptane/DCM gradient as eluent). The desired fractions were collected and concentrated in vacuo to yield intermediate compound D7 (1.1 g, 33%).
Workup
- customThe resulting reaction mixture
- temperaturewas gradually warmed to room temperature
- stirringstirred for 1 h
- customThe reaction mixture was quenched with water
- extractionextracted with Et2O
- customThe organic layer was separated
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
- customThe crude product was purified by column chromatography (silica gel; Heptane/DCM gradient as eluent)
- customThe desired fractions were collected
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-d68676c6327241b5bad5fb94f9f2b678
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946205B2
Reaction notes
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