Acetic Anhydride → HCID 58566553, compound
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:11][OH:12])(C)[CH2:7][C:6]=2[CH:13]=1.C(N(CC)CC)C.[C:21](OC(=O)C)(=[O:23])[CH3:22]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:21]([O:12][CH2:11][CH:8]1[CH2:7][C:6]2[CH:13]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:9]1)(=[O:23])[CH3:22]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
To an ice cold solution of (5-fluoro-2-methyl-2,3-dihydrobenzofuran-2-yl)methanol (854) (0.530 g, 3.15 mmol) in DCM (3.2 mL) was added triethylamine (0.878 mL, 6.3 mmol), DMAP (0.077 g, 0.63 mmol) and acetic anhydride (0.222 mL, 2.4 mmol). The solution was stirred at 0° C. for 2 h. The layers were separated and washed with water (2×5 mL), 1N HCl (5 mL), brine (100 mL) and dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography (0-10% EtOAc in hexanes) to provide the desired (5-fluoro-2,3-dihydrobenzofuran-2-yl)methyl acetate (866) (0.530 g, 80.0%) as a colorless oil.
Workup
- customThe layers were separated
- washwashed with water (2×5 mL), 1N HCl (5 mL), brine (100 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by chromatography (0-10% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-32cb20fe420c4d73ae87eee13989c6c6
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476308B2
Reaction notes
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