Acrylic acid, 2-(hydroxymethyl)-, ethyl ester → Ethyl 2-(fluoromethyl)prop-2-enoate

HRID 1038024Notes

Reaction equation

HRID 1038024 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

4

Reactant 2

HCID 24827Acrylic acid, 2-(hydroxymethyl)-, ethyl esterHCID 123472(Diethylamino)sulfur trifluoride2×

Product 1

HCID 12815505Ethyl 2-(fluoromethyl)prop-2-enoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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

  1. additionwas added
  2. customreaction
  3. temperatureto warm to room temperature
  4. customquenched with saturated sodium carbonate
  5. customOrganic layer was isolated
  6. washwashed with water, brine
  7. dry with materialdried (MgSO4)
  8. washeluted with dichloromethane
  9. customthe product fractions were collected
  10. customThe combined fractions (ca. 12 ml) will be directly used in the next step synthesis without further concentration

Sources & evidence

ORD record
ord-df81805611544e569bb2cb8f0cebd729
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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