Dimethyl Sulfoxide → HCID 10944542, compound

HRID 1707874Notes

Reaction equation

HRID 1707874 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([O:18][C@@H:19]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:20][OH:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O[C@@H](CC1C=CC=CC=1)C(O)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(N(CC)CC)C>C(Cl)Cl.O>[CH2:11]([O:18][C@@H:19]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:20][OH:21])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1.[CH2:11]([O:18][C@@H:19]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH:20]=[O:21])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

10

Reactant 6

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 4447183-Phenyllactic acid, (S)-HCID 11831604HCID 11831604, compoundHCID 21226445Aluminium lithium hydride

Product 2

HCID 10944542HCID 10944542, compoundHCID 11831604HCID 11831604, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Under anhydrous conditions, dry dimethylsulfoxide (3.23 mL, 45.5 mmol) was added dropwise over a 10 min period to a stirred solution of oxalyl chloride (2.52 mL, 28.9 mmol) in dry CH2Cl2 (155 mL) at -78°. After another 10 min, a solution of (S)-2-Benzyloxy-3-phenylpropanol (5.00 g, 20.7 mmol) in CH2Cl2 (52 mL) was added dropwise over 20 min to the preceding solution at -78°. [(S)-2-Benzyloxy-3-phenylpropanol is prepared from the commercially available (S)-2-hydroxy-3-phenylpropionic acid by benzylation followed by lithium aluminium hydride reduction.] The resultant mixture was stirred at -78° for 30 min. Thereafter, triethylamine (14.41 mL, 103.3 mmol) was added rapidly to the mixture. The resulting mixture was diluted with H2O and extracted with EtOAc. The EtOAc extract was washed sequentially with a saturated aqueous solution of NH4Cl, water and brine, dried (MgSO4) and evaporated to dryness to give (S)-2-Benzyloxy-3-phenylpropanal.

Workup

  1. extractionextracted with EtOAc
  2. extractionThe EtOAc extract
  3. washwas washed sequentially with a saturated aqueous solution of NH4Cl, water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-fc1d4e54586c4b908596dfce56d116cb
Source dataset
uspto-grants-1994_10
Patent number
US05354767

Reaction notes

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