4-Toluenesulfonyl chloride → (R)-(2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)methyl 4-methylbenzenesulfonate

HRID 453838노트

반응식

HRID 453838 반응식
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@@H:2]1[CH2:11][OH:12].C(N(CC)CC)C.[C:20]1([CH3:30])[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(Cl)Cl>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][C@@H:2]1[CH2:11][O:12][S:26]([C:23]1[CH:24]=[CH:25][C:20]([CH3:30])=[CH:21][CH:22]=1)(=[O:28])=[O:27]

참가 물질

5

반응물 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 676612(S)-(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanol

생성물 1

HCID 7101148(R)-(2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)methyl 4-methylbenzenesulfonate수율 99.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

(S)-1-(2,3-Dihydro-benzo[1,4]dioxin-2-yl)-methanol (24.1 mmol, 4.0 g), triethylamine (24.3 mmol, 3.42 ml) and DCM (50 ml) were mixed and stirred on an ice-bath. p-Toluenesulfonyl chloride (24.3 mmol, 4.63 g) in DCM (10 ml) was added dropwise. The mixture was stirred over night at r.t and washed with water. The organic phase was evaporated to dryness. The crude product was dissolved in THF (10 ml) and treated with 1 M NaOH (2 ml) for 10 minutes. Water (100 ml) was added. The aqueous solution was extracted with EtOAc, the organic phase was dried and evaporated to dryness. Flash chromatography, using heptane/EtOAc as eluent gave 7.66 g of the desired product.

후처리

  1. stirringThe mixture was stirred over night at r.t
  2. washwashed with water
  3. customThe organic phase was evaporated to dryness
  4. dissolutionThe crude product was dissolved in THF (10 ml)
  5. additiontreated with 1 M NaOH (2 ml) for 10 minutes
  6. additionWater (100 ml) was added
  7. extractionThe aqueous solution was extracted with EtOAc
  8. customthe organic phase was dried
  9. customevaporated to dryness

출처 및 근거

ORD 기록
ord-d8c24071dbf84b5ba05b9893033598ad
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492549B2

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