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

HRID 453838

反応式

HRID 453838 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-d8c24071dbf84b5ba05b9893033598ad
出典データセット
uspto-grants-2013_07
特許番号
US08492549B2

関連ノート

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