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Potassium Phosphate, Tribasic → (7-benzenesulfonyl-2,3-dihydro-benzo[1,4]dioxin-2(R)-yl)-methanol

HRID 2221308
Notes
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Reaction equation

HRID 2221308 reaction equation
[C:1]1([S:7]([C:10]2[CH:21]=[CH:20][C:13]([O:14][CH2:15][C@H:16]([OH:19])[CH2:17][OH:18])=[C:12](Br)[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:1]1([S:7]([C:10]2[CH:21]=[CH:20][C:13]3[O:14][CH2:15][C@@H:16]([CH2:17][OH:18])[O:19][C:12]=3[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphineHCID 68527750HCID 68527750, compound

Product 1

HCID 59710879(7-benzenesulfonyl-2,3-dihydro-benzo[1,4]dioxin-2(R)-yl)-methanol

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetate
Catalyst
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 3-(4-benzenesulfonyl-2-bromo-phenoxy)-propane 1-2-(R)-diol (0.390 g, 0.001 mol), Pd(OAc)2 (0.007 g, 0.00003 mol, 3 mol %), racemic-2-(di-t-butylphosphino)-1,1′-binaphthyl (0.012 g, 0.00003, 3 mol %) and K3PO4 (0.320 g, 0.0015, 1.5 equiv) in toluene (1 mL) was heated under argon atmosphere at 80° C. for 5 hours. After cooling to ambient temperature the mixture was diluted with ethyl acetate (1 mL), washed with water and saturated sodium chloride, dried (Na2SO4) and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel (eluting with hexane-ethyl acetate; 1:1, v/v) to give (7-benzenesulfonyl-2,3-dihydro-benzo[1,4]dioxin-2(R)-yl)-methanol as an oil which solidified upon standing. (0.160 g; 52%). m. p. 112.0-113.5° C., [α]=+36.7° (CHCl3, c=1).

Workup

  1. temperatureAfter cooling to ambient temperature the mixture
  2. washwashed with water and saturated sodium chloride
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography on silica gel (
  6. washeluting with hexane-ethyl acetate

Sources & evidence

ORD record
ord-d53fb7f40caf4ef786b0664e147bc056
Source dataset
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07368567B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes