Dichloromethane → HCID 86650568, compound

HRID 243663Notes

Reaction equation

HRID 243663 reaction equation
C([C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:6][C:5]([CH3:15])([CH3:14])[N:4]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=O.C1(P(=[CH:42][CH:43]=[O:44])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:45](Cl)Cl>>[CH3:14][C:5]1([CH3:15])[N:4]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[C@H:3](/[CH:45]=[CH:42]/[CH:43]=[O:44])[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:6]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 75051(Triphenylphosphoranylidene)acetaldehydeHCID 9972368HCID 9972368, compound

Product 1

HCID 86650568HCID 86650568, compoundYield 72%

Procedure

To a solution of tert-butyl (4S,5R)-4-formyl-2,2-dimethyl-5-phenyl-1,3-oxazolidine-3-carboxylate (20.9, 89.1 mmol) in CH2Cl2 (150 mL) was added (triphenylphosphoranylidene) acetaldehyde (27.1 g, 89.1 mmol) and the resulting mixture was stirred at ambient temperature for 40 h. After removal of ⅓ of the solvent, hexanes was generously added and the resulting solid was filtered off. Flash chromatography on a Biotage Horizon® system (silica gel, 0 to 20% ethyl acetate in hexanes gradient then 20% ethyl acetate in hexanes) gave 16.3 g (72%) of the title compound as a yellow oil. LC/MS 354.3 (M+23).

Workup

  1. customAfter removal of ⅓ of the solvent, hexanes
  2. additionwas generously added
  3. filtrationthe resulting solid was filtered off

Sources & evidence

ORD record
ord-a58987cd1a0a49c08e9e355bd1d161f4
Source dataset
uspto-grants-2014_02
Patent number
US08653260B2

Reaction notes

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