Acetic Anhydride → HCID 54487648, compound

HRID 1858035Notes

Reaction equation

HRID 1858035 reaction equation
[CH3:1][C:2]1([CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([CH3:14])[C:6]([CH3:13])=[C:7](O)[CH:8]=2)[O:3]1.[C:20](OC(=O)C)(=[O:22])[CH3:21]>N1C=CC=CC=1>[CH3:1][C:2]1([CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([CH3:14])[C:6]([CH3:13])=[C:7]([C:20](=[O:22])[CH3:21])[CH:8]=2)[O:3]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 1330982,7,8-Trimethyl-2-(beta-carboxy-ethyl)-6-hydroxychroman

Product 1

HCID 54487648HCID 54487648, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Racemic 2,7,8-Trimethyl-2-(β-carboxyethyl)-6-hydroxy chroman (500 mg) (see Example 11) was dissolved in pyridine (20 mL) at room temperature, and acetic anhydride (10 mL) was added. The solution was maintained at room temperature for 5 hours, solvent was removed under vacuum, methanol (4×10 mL) was added and then removed under reduced pressure. The residual oil was dissolved in ethyl acetate (150 mL) and the organic phase was washed with water (50 mL), aqueous HCl (1 N, 50 mL) and water (50 mL), then dried over sodium sulfate. Solvent was then removed, and the residual oily material was purified on a silica gel column with hexane/ethyl acetate (1:1). The desired product crystallized from acetone/hexane, m.p. 105-107° C.

Workup

  1. customsolvent was removed under vacuum, methanol (4×10 mL)
  2. additionwas added
  3. customremoved under reduced pressure
  4. dissolutionThe residual oil was dissolved in ethyl acetate (150 mL)
  5. washthe organic phase was washed with water (50 mL), aqueous HCl (1 N, 50 mL) and water (50 mL)
  6. dry with materialdried over sodium sulfate
  7. customSolvent was then removed
  8. customthe residual oily material was purified on a silica gel column with hexane/ethyl acetate (1:1)
  9. customThe desired product crystallized from acetone/hexane, m.p. 105-107° C.

Sources & evidence

ORD record
ord-6a0bcd510479457ea544f2150c87af76
Source dataset
uspto-grants-2000_11
Patent number
US06150402

Reaction notes

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