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Water → Methanesulfonic acid (S)-3-(2,6-dihydroxy-phenoxy)-2-methanesulfonyloxy-propyl ester

HRID 453833
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HRID 453833 반응식
C[O:2][C:3]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23]C)[C:4]=1[O:5][CH2:6][C@H:7]([O:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH2:8][O:9][S:10]([CH3:13])(=[O:12])=[O:11].B(Br)(Br)Br.O>ClCCl>[OH:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:3]([OH:2])[C:4]=1[O:5][CH2:6][C@H:7]([O:14][S:15]([CH3:18])(=[O:16])=[O:17])[CH2:8][O:9][S:10]([CH3:13])(=[O:11])=[O:12]
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참가 물질

5

반응물 3

HCID 962WaterHCID 25134Boron tribromideHCID 86644725Methanesulfonic acid (S)-3-(2,6-dimethoxy-phenoxy)-2-methanesulfonyloxy-propyl ester

생성물 1

HCID 86644726Methanesulfonic acid (S)-3-(2,6-dihydroxy-phenoxy)-2-methanesulfonyloxy-propyl ester수율 88.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Methanesulfonic acid (S)-3-(2,6-dimethoxy-phenoxy)-2-methanesulfonyloxy-propyl ester (3.08 g, 8.00 mmol) in) in dichloromethane (40 ml) was cooled to 0° C. and stirred under nitrogen atmosphere. Boron tribromide (1 M solution in dichloromethane, 18 ml, 18 mmol) was added in 15 min. The mixture was stirred at +25° C. for 4 h, and poured on mixture of ice (10 g) and water (15 ml), and the layers were separated. Organic phase was recovered and water layer was extracted twice with dichloromethane (15 ml). Organic phase and dichloromethane extracts were combined and washed with water (15 ml) and saturated sodium chloride solution (15 ml). The combined organic phase was dried (Na2SO4), filtered and evaporated to dryness to give 2.53 g of the title compound.

후처리

  1. stirringThe mixture was stirred at +25° C. for 4 h
  2. customthe layers were separated
  3. customOrganic phase was recovered
  4. extractionwater layer was extracted twice with dichloromethane (15 ml)
  5. washwashed with water (15 ml) and saturated sodium chloride solution (15 ml)
  6. dry with materialThe combined organic phase was dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated to dryness

출처 및 근거

ORD 기록
ord-658c3db8ade74e4dae2b04253f93081a
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08492549B2

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