Acrylic acid, 2-(hydroxymethyl)-, ethyl ester → Ethyl 2-(fluoromethyl)prop-2-enoate
Reaction equation
C(N(S(F)(F)[F:7])CC)C.[CH2:10]([O:12][C:13](=[O:18])[C:14]([CH2:16]O)=[CH2:15])[CH3:11]>ClCCl>[CH2:10]([O:12][C:13](=[O:18])[C:14]([CH2:16][F:7])=[CH2:15])[CH3:11]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (diethylamino)sulfur trifluoride (DAST) (363 μl, 2.76 mmol) in dichloromethane (1 ml) was slowly added at −78 C. a solution of 2-hydroxylmethyl acrylic acid ethyl ester (300 mg, 2.31 mmol) in dichloromethane (3 ml). The reaction mixture was allowed to warm to room temperature, re-chilled to −78 C. and additional DAST (100 μl, 0.76 mmol) was added to ensure complete reaction. The reaction mixture was let to warm to room temperature and quenched with saturated sodium carbonate. Organic layer was isolated, washed with water, brine and dried (MgSO4). The dichloromethane solution was directly passed through a short silica gel pad, eluted with dichloromethane and the product fractions were collected. The combined fractions (ca. 12 ml) will be directly used in the next step synthesis without further concentration.
Workup
- temperaturere-chilled to −78 C
- customreaction
- temperatureto warm to room temperature
- customquenched with saturated sodium carbonate
- customOrganic layer was isolated
- washwashed with water, brine
- dry with materialdried (MgSO4)
- washeluted with dichloromethane
- customthe product fractions were collected
- customThe combined fractions (ca. 12 ml) will be directly used in the next step synthesis without further concentration
Sources & evidence
- ORD record
- ord-e915da04bca04077bb4b0f2c2edcd6b5
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07807672B2
Reaction notes
Loading…