Dimethylformamide → Benzyl (S)-(-)-2-hydroxy-3-phenylpropionate

HRID 1886522Notes

Reaction equation

HRID 1886522 reaction equation
[C:1](=[O:4])(O)[O-:2].[Na+].[CH2:6](Br)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CN(C)[CH:16]=[O:17]>>[OH:17][C@@H:16]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:1]([O:2][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 7498Benzyl BromideHCID 516892Sodium Bicarbonate

Product 1

HCID 10377698Benzyl (S)-(-)-2-hydroxy-3-phenylpropionate

Conditions

Temperature
25 °C

Procedure

To mixture of the title A compound (9.97 g, 60 mmols) and sodium bicarbonate (10 g, 120 mmols) in dimethyformamide (50 mL) was added a solution of benzyl bromide (7.13 mL, 60 mmols) in dimethylformamide (10 mL). The mixture was stirred at 25° C. under argon for 48 hours, after which it was concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with water, saturated sodium bicarbonate solution, and brine, dried over anhydrous magnesium sulfate, and concentrated. The residue (12.7 g) was chromatographed on silica gel (eluting with 4:1 hexane:ethyl acetate) to give 12 g of the title B compound.

Workup

  1. concentrationafter which it was concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water, saturated sodium bicarbonate solution, and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue (12.7 g) was chromatographed on silica gel (eluting with 4:1 hexane:ethyl acetate)
  7. customto give 12 g of the title B compound

Sources & evidence

ORD record
ord-339729f71651482196203a9685b1c964
Source dataset
uspto-grants-1992_09
Patent number
US05151513

Reaction notes

Loading…