Lithium hydroxide, monohydrate → HCID 59333716, compound

HRID 1930729Notes

Reaction equation

HRID 1930729 reaction equation
[F:1][CH2:2][CH:3]([O:6][CH2:7][C:8]([O:10]CC1C=CC=CC=1)=[O:9])[CH2:4][F:5].O.[OH-].[Li+]>C1COCC1.O>[F:1][CH2:2][CH:3]([O:6][CH2:7][C:8]([OH:10])=[O:9])[CH2:4][F:5]

Participants

5

Procedure

Benzyl 2-(1,3-difluoropropan-2-yloxy)acetate (0.91 g, 3.73 mmol) was dissolved in THF (14 mL)/water (7 mL) mixture and treated with lithium hydroxide monohydrate (0.469 g, 11.18 mmol) and allowed to stir for 16 hours at room temperature. The mixture was concentrated, redissolved in water and extracted with ethyl acetate. The aqueous phase was treated with 2M HCl and NaCl then extracted with ethyl acetate (3×). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to afford the title product (0.388 g, 67% yield).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionredissolved in water
  3. extractionextracted with ethyl acetate
  4. additionThe aqueous phase was treated with 2M HCl and NaCl
  5. extractionthen extracted with ethyl acetate (3×)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-324763c68e9b4012a214af574076c7ed
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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