Tetrabutylammonium Fluoride → (E)-4-(3,4-dichlorophenyl)but-3-en-1-ol
Reaction equation
C([Si]([O:8][CH2:9][CH2:10]/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([Cl:20])[CH:14]=1)(C)C)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)(=O)C>[Cl:20][C:15]1[CH:14]=[C:13](/[CH:12]=[CH:11]/[CH2:10][CH2:9][OH:8])[CH:18]=[CH:17][C:16]=1[Cl:19]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To solution of Intermediate 2A (2.2 g, 5.2 mmol) in THF (50 mL) cooled to 0° C. was added TBAF (6.3 mL, 6.3 mmol) via dropwise addition. The reaction mixture was stirred at 0° C. for 1 h, then diluted with ethyl acetate (200 mL). The organic layer was washed with water (2×100 mL), dried over Na2SO4 and dried in vacuo. The product was purified by silica gel chromatography (80 g silica gel; linear gradient 0-25% ethyl acetate for 30 min) to obtain 917 mg (97% yield) of Intermediate 2B. HPLC/MS (Method D) RT=1.00 min, [M−H2O+1]+ 199.1.
Workup
- additionvia dropwise addition
- washThe organic layer was washed with water (2×100 mL)
- dry with materialdried over Na2SO4
- customdried in vacuo
- customThe product was purified by silica gel chromatography (80 g silica gel; linear gradient 0-25% ethyl acetate for 30 min)
Sources & evidence
- ORD record
- ord-dead891eb8c54e5fac10f2035ff3cdaf
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08952180B2
Reaction notes
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