Dimethyl Sulfoxide → 6-((benzyloxy)methyl)dihydro-2H-pyran-3(4H)-one

HRID 405781

반응식

HRID 405781 반응식
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([O:18][CH2:19][CH:20]1[O:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C.[NH4+].[Cl-]>ClCCl>[CH2:11]([O:18][CH2:19][CH:20]1[O:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

참가 물질

7

반응물 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 580637066-(benzyloxymethyl)tetrahydro-2H-pyran-3-ol

생성물 1

HCID 580636326-((benzyloxy)methyl)dihydro-2H-pyran-3(4H)-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

DMSO (1.15 mL, 16.2 mmol) was added to a stirred solution of oxalyl chloride (1 mL, 10.8 mmol) in dichloromethane (60 mL) at −78° C. After 10 minutes, a dichloromethane solution of 6-(benzyloxymethyl)tetrahydro-2H-pyran-3-ol (14) (1.20 g, 5.40 mmol) was added. Stirring was continued for one hour then triethylamine (3.8 mL, 27 mmol) was added and slowly warmed to 0° C. The reaction was poured into saturated NH4Cl solution and the organic phase was washed with brine and dried (NaSO4). The residue was purified over silica gel using EtOAc and hexanes to give 6-(benzyloxymethyl)dihydro-2H-pyran-3(4H)-one (15).

후처리

  1. waitwas continued for one hour
  2. washthe organic phase was washed with brine
  3. dry with materialdried (NaSO4)
  4. customThe residue was purified over silica gel

출처 및 근거

ORD 기록
ord-3663cbdaaeb047ac91dd5d57d64ae722
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754071B2

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