Acetic Acid → HCID 13861701, compound
Reaction equation
C([Li])(CC)C.[C:6]([Si:10]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)([CH3:12])[CH3:11])([CH3:9])([CH3:8])[CH3:7].B(OC)(OC)[O:23]C.CC(O)=O.OO>C1COCC1.C(OCC)C>[Si:10]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([OH:23])[CH:16]=1)([C:6]([CH3:9])([CH3:7])[CH3:8])([CH3:12])[CH3:11]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
sec-Butyllithium (20.7 mL, 29.0 mmol) was added dropwise to a solution of tert-butyl(4-fluorobenzyloxy)dimethylsilane (2) (6.33 g, 26.3 mmol) in THF (30 mL) over 30 min, at −78° C. Trimethyl borate (2.99 mL, 26.3 mmol) was added dropwise over 30 min while the temperature was maintained at −78° C. The reaction mixture was allowed to warm to 0° C. and AcOH (2.26 mL, 39.5 mmol) was added dropwise, followed by hydrogen peroxide (2.48 mL, 29.0 mmol). The mixture was stirred at 0° C. for 30 min then allowed to warm to RT and stirred for 1 h. The reaction mixture was diluted with diethyl ether (100 mL) and washed with 2M NaOH (100 mL) and brine (100 mL). The organic solution was dried over MgSO4, filtered and the solvent was removed in vacuo to give 5-((tert-butyldimethylsilyloxy)methyl)-2-fluorophenol (3) (4.0 g, 50%) as a colourless oil: m/z 255 [M−H]− (ES−).
Workup
- temperatureto warm to 0° C.
- temperatureto warm to RT
- stirringstirred for 1 h
- washwashed with 2M NaOH (100 mL) and brine (100 mL)
- dry with materialThe organic solution was dried over MgSO4
- filtrationfiltered
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-e64194a762cc4935b9b6faeb1d5be5fa
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447028B2
Reaction notes
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