三苯基膦 → 2-Chlorobenzenesulfonic acid 3-[(3-cyanophenyl)methoxy]phenyl ester

HRID 368545

反应方程式

HRID 368545 反应方程式
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:15]=[C:16]([O:20][S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])(=[O:23])=[O:22])[CH:17]=[CH:18][CH:19]=1.[C:31]([C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH2:36]O)#[N:32].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[C:31]([C:33]1[CH:34]=[C:35]([CH2:36][O:13][C:14]2[CH:15]=[C:16]([O:20][S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])(=[O:23])=[O:22])[CH:17]=[CH:18][CH:19]=2)[CH:38]=[CH:39][CH:40]=1)#[N:32]

参与物

5

反应物 4

HCID 11776三苯基膦HCID 220568偶氮二甲酸二乙酯HCID 27346773-羟甲基苯甲腈HCID 540152812-Chlorobenzenesulfonic acid 3-hydroxyphenyl ester

产物 1

HCID 538328372-Chlorobenzenesulfonic acid 3-[(3-cyanophenyl)methoxy]phenyl ester收率 93.8%

反应条件

温度
0 °C

实验过程

Diethyl azodicarboxylate (174 mg, 1.0 mmol) was added to a solution of 2-chlorobenzenesulfonic acid 3-hydroxyphenyl ester (285 mg, 1.0 mmol), as prepared in the preceding step, 3-cyanobenzyl alcohol (133 mg, 1.0 mmol)(Yoon et al., J. Org. Chem. 38:2786-2792 (1973)), and triphenylphosphine (263 mg, 1.0 mmol) in tetrahydrofyiran (10 mL) at 0° C. The mixture was stirred at 0° C. for 2 hours and at room temperature for 3 hours. The reaction mixture was quenched with water (30 mL) and extracted with ethyl acetate (3×30 mL). The organic phase was washed with saturated NaHCO3 (2×30 mL), brine (2×30 mL) and dried over Na2SO4. The solvent was removed in vacuo the residue was purified by flash column chromatography (2:1 ethyl acetate:hexane) to give the title compound as a pale yellow oil (375 mg, 93%). 1H-NMR (300 MHz, CDCl3) δ 5.02 (s, 2 H), 6.78 (m, 2H), 6.85 (dd, 1H, J=4.2, 1.3 Hz), 7.20 (t, 1H, J=8.2 Hz), 7.38 (t, 1H, J=5.8 Hz), 7.51 (t, 1H, J=7.7 Hz), 7.59-7.68 (m, 5 H) and 7.93 (dd, 1 H, J=4.0, 0.7 Hz).

后处理

  1. customThe reaction mixture was quenched with water (30 mL)
  2. extractionextracted with ethyl acetate (3×30 mL)
  3. washThe organic phase was washed with saturated NaHCO3 (2×30 mL), brine (2×30 mL)
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo the residue
  6. customwas purified by flash column chromatography (2:1 ethyl acetate:hexane)

来源与证据

ORD记录
ord-12ba5f6eaf2c48cca20c70c4f484b29f
来源数据集
uspto-grants-2000_10
专利号
US06133315

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