Water → 5-(Benzyloxy)-2-(chloromethyl)-3,4-dihydronaphthalene

HRID 1271269노트

반응식

HRID 1271269 반응식
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][C:13]([CH2:19]O)=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S([Cl:30])(=O)=O)=CC=1.C(N(CC)CC)C.O>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][C:13]([CH2:19][Cl:30])=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 229320215-(Benzyloxy)-2-(hydroxymethyl)-3,4-dihydronaphthalene

생성물 1

HCID 229320295-(Benzyloxy)-2-(chloromethyl)-3,4-dihydronaphthalene수율 54.5%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

Under an argon atmosphere, to a solution of 1.82 g of 5-(benzyloxy)-2-(hydroxymethyl)-3,4-dihydronaphthalene and 0.55 g of 4-(dimethylamino)pyridine in 30 ml of dichloromethane, 1.43 g of p-toluenesulfonyl chloride was added. After 1.2 ml of triethylamine was added dropwise, the mixture was stirred at room temperature for 1.5 hours. The reaction solution was poured into iced water and then extracted with diethyl ether. The extract was washed in turn with 5% hydrochloric acid, water and an aqueous saturated sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.06 g of the desired compound as a colorless oily substance.

후처리

  1. extractionextracted with diethyl ether
  2. washThe extract was washed in turn with 5% hydrochloric acid, water
  3. dry with materialan aqueous saturated sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-86fa57b7215a4f6eb1838bf422b7b0c7
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07205302B2

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