Dimethyl Sulfoxide → HCID 86665265, compound

HRID 918984Notes

Reaction equation

HRID 918984 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Si:11]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][C@@H:33]1[O:35][C@@H:34]1[CH2:36][OH:37])([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[Si:11]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][C@@H:33]1[O:35][C@@H:34]1[CH:36]=[O:37])([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86665266HCID 86665266, compound

Product 1

HCID 86665265HCID 86665265, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Dry DMSO (114 mg, 0.4 mmol) was added dropwise to a stirring, −80° C. solution of oxalyl chloride (110 mg, 0.3 mmol) in dry CH2Cl2 (10 mL) under an argon atmosphere. After 20 min, a solution of ((2R,3S)-3-(4-(tert-butyldiphenylsilyloxy)butyl)oxiran-2-yl)methanol (200 mg, 0.1 mmol) in dry CH2Cl2 (50 mL) was added slowly. After 45 min, triethylamine (200 mg, 0.5 mmol) was added and the reaction mixture was warmed to 0° C. After 0.5 h, the reaction mixture was quenched with water (50 mL). The aqueous layer was separated and back-extracted with CH2Cl2 (2×10 mL). The combined organic extracts were washed with water, brine, and dried over anhydrous Na2SO4, and evaporated in vacuo. The residue was purified via SiO2 column chromatography using 5% EtOAc/hexanes to give (2S,3S)-3-[4-(tert-butyldiphenylsilanyloxy)-butyl]-oxirane-2-carbaldehyde. The crude aldehyde was used for the next reaction without further purification.

Workup

  1. waitAfter 45 min
  2. waitAfter 0.5 h
  3. customthe reaction mixture was quenched with water (50 mL)
  4. customThe aqueous layer was separated
  5. extractionback-extracted with CH2Cl2 (2×10 mL)
  6. washThe combined organic extracts were washed with water, brine
  7. dry with materialdried over anhydrous Na2SO4
  8. customevaporated in vacuo
  9. customThe residue was purified via SiO2 column chromatography

Sources & evidence

ORD record
ord-d9e10698bee74f49a5492d1cdec26599
Source dataset
uspto-grants-2016_03
Patent number
US09272991B2

Reaction notes

Loading…