Solketal → (2,2-Dimethyl-1,3-dioxolan-4-yl)methyl butyrate
Reaction equation
[CH3:1][C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.CCN(CC)CC.[CH3:17][CH2:18][CH2:19][C:20](Cl)=[O:21]>CN(C1C=CN=CC=1)C.COC(C)(C)C.CCOC(C)=O>[C:20]([O:8][CH2:7][CH:5]1[CH2:4][O:3][C:2]([CH3:9])([CH3:1])[O:6]1)(=[O:21])[CH2:19][CH2:18][CH3:17]Participants
7
Conditions
- Temperature
- 0 °C
Procedure
To a well-stirred solution of solketal (21, 62.6 ml, 500 mmol), Et3N (83.6 ml, 600 mmol) and DMAP (5 g, 40.9 mmol) in tert-butyl methyl ether (11) at 0° C., n-butyryl chloride (52.4 mL, 500 mmol) was added dropwise over a 75 minute period. The mixture was stirred for an additional hour at 0° C. and then at room temperature for an additional 5 hours. The mixture was diluted with AcOEt (11), washed with water (11), dried (MgSO4), filtered and evaporated to afford 22 (104.6 g, 500 mmol, 100%) as an oil. The material was used in the next step without any further purification.
Workup
- washwashed with water (11)
- dry with materialdried (MgSO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-7644401fcdec48a680ce1003a6ee26e6
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06215004B1
Reaction notes
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