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Triethylamine → Methanesulfonic acid 1-naphthalen-1-yl-cyclopentylmethyl ester

HRID 2169376
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HRID 2169376 반응식
[C:1]1([C:11]2([CH2:16][OH:17])[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[S:25](Cl)([CH3:28])(=[O:27])=[O:26].C(OCC)(=O)C>ClCCl.CCCCCC>[C:1]1([C:11]2([CH2:16][O:17][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1
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참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 86726005(1-Naphthalen-1-yl-cyclopentyl)-methanol

생성물 1

HCID 86726006Methanesulfonic acid 1-naphthalen-1-yl-cyclopentylmethyl ester수율 35%

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
2회
HCID 8058Hexane용매

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온도
0 °C

실험 절차

To a solution of (1-naphthalen-1-yl-cyclopentyl)-methanol (340) (9.0 g, 39.8 mmol) in dichloromethane (180 mL) was added triethylamine (11.0 mL, 79.5 mL) and the reaction mixture was cooled to 0° C. To this reaction mixture was added mesylchloride and stirring was continued at room temperature for 18 h (silica TLC, 10% ethyl acetate in hexane; Rf=0.2). The reaction mass was diluted with dichloromethane (100 mL), washed with water (2×100 mL) and brine (100 mL) and dried and concentrated in vacuum to get a crude mass which was purified by Combi-Flash using gradient eluent mixture of ethyl acetate and hexane to get pure methanesulfonic acid 1-naphthalen-1-yl-cyclopentylmethyl ester (341) (4.25 g, 35%) as a white solid.

후처리

  1. washwashed with water (2×100 mL) and brine (100 mL)
  2. customdried
  3. concentrationconcentrated in vacuum
  4. customto get a crude mass which
  5. customwas purified by Combi-Flash
  6. additiongradient eluent mixture of ethyl acetate and hexane

출처 및 근거

ORD 기록
ord-f83c01625bf04d02949a4f2082ed7ef1
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09045486B2

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