Acetic Anhydride → HCID 22005239, compound
Reaction equation
[CH:1]([C:4]1[C:9]([CH2:10][O:11][Si:12]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:8]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C:7]([CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[C:6]([CH3:41])[N+:5]=1[O-])([CH3:3])[CH3:2].[C:43]([O:46]C(=O)C)(=[O:45])[CH3:44]>>[C:43]([O:46][CH2:41][C:6]1[C:7]([CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[C:8]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[C:9]([CH2:10][O:11][Si:12]([C:25]([CH3:26])([CH3:28])[CH3:27])([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[C:4]([CH:1]([CH3:2])[CH3:3])[N:5]=1)(=[O:45])[CH3:44]Participants
3
Conditions
- Temperature
- 100 °C
Procedure
A mixture of the intermediate obtained in Example 199, Step B (4.8 g, 7.97 mmol) and acetic anhydride (20 mL) was heated to 100° C. for 20 min. The mixture was poured onto ice and the aqueous phase extracted with ethyl acetate (3×30 mL). The combined organic phase was washed with saturated aqueous sodium bicarbonate solution (3×50 mL), and saturated aqueous sodium chloride solution (3×50 mL). Silica gel chromatography provided a yellow oil (4.4 g, 90%). 1H NMR (300 MHz, CDCl3): δ 7.40 (m, 6H), 7.31 (m, 4H), 7.06 (m, 4H), 5.29 (s, 2H), 4.26 (s, 2H), 3.14 (sept, 6.8 Hz, 1H), 2.2 (m, 2H), 2.18 (s, 3H), 1.2 (m, 2H), 1.16 (d, 6.6 Hz, 6H), 1.05 (m, 4H), 0.99 (s, 9H), 0.77 (t, 6.8 Hz, 3H).
Workup
- additionThe mixture was poured onto ice
- extractionthe aqueous phase extracted with ethyl acetate (3×30 mL)
- washThe combined organic phase was washed with saturated aqueous sodium bicarbonate solution (3×50 mL), and saturated aqueous sodium chloride solution (3×50 mL)
Sources & evidence
- ORD record
- ord-0cfd936c8f4a4ad2a43f1d4cea168353
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06218431B1
Reaction notes
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