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

HRID 2221308Notes

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

Participants

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

temperatureAfter cooling to ambient temperature the mixture
washwashed with water and saturated sodium chloride
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customThe crude material was purified by flash chromatography on silica gel (
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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