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

HRID 2221308
ノート
印刷プレビュー

反応式

HRID 2221308 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒
HCID 1140
Toluene
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d53fb7f40caf4ef786b0664e147bc056
出典データセット
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07368567B2

反応ノート

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