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

HRID 2366041
Notes
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Reaction equation

HRID 2366041 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f01c8b76b15a48828694d8ad6e3ae32f
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08697723B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes