Triethylamine → Methyl 2-[(4-{2-[(methylsulfonyl)oxy]ethyl}phenoxy)methyl]benzoate

HRID 2111998

反応式

HRID 2111998 の反応式
[OH:1][CH2:2][CH2:3][C:4]1[CH:21]=[CH:20][C:7]([O:8][CH2:9][C:10]2[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=2[C:12]([O:14][CH3:15])=[O:13])=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>ClCCl>[CH3:29][S:30]([O:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]2[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=2[C:12]([O:14][CH3:15])=[O:13])=[CH:20][CH:21]=1)(=[O:32])=[O:31]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58820416Methyl 2-{[4-(2-hydroxyethyl)phenoxy]methyl}benzoate

生成物 1

HCID 86601923Methyl 2-[(4-{2-[(methylsulfonyl)oxy]ethyl}phenoxy)methyl]benzoate収率 46%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-20 °C

実験手順

Methyl 2-{[4-(2-hydroxyethyl)phenoxy]methyl}benzoate (1.2 g, 4.19 mmol) was dissolved in dichloromethane (20 ml) and the solution was cooled to −20° C. Triethylamine (0.64 g, 6.29 mmol) was added dropwise, and then methylsulfonyl chloride (0.53 g, 4.61 mmol) was added dropwise. The ice bath was removed and the mixture was stirred at room temperature for one hour. Diethyl ether (5 ml) was added and the precipitate was filtered off. The organic phase was washed with 2 portions of brine, dried (MgSO4) and the solvent was removed by evaporation. The crude was purified by preparative HPLC (starting with acetonitrile/buffer 60/40 and then the acetonitrile concentration was increased to 100%, the buffer was a mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min). The product containing fractions were pooled and the acetonitrile was removed by evaporation. EtOAc (10 ml) was added and the organic phase was washed with two portions of brine and dried (MgSO4). This gave 0.703 g of methyl 2-[(4-{2-[(methylsulfonyl)oxy]ethyl}phenoxy)-methyl]benzoate (yield 46%).

後処理

  1. customThe ice bath was removed
  2. additionDiethyl ether (5 ml) was added
  3. filtrationthe precipitate was filtered off
  4. washThe organic phase was washed with 2 portions of brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent was removed by evaporation
  7. customThe crude was purified by preparative HPLC (
  8. concentrationthe acetonitrile concentration
  9. temperaturewas increased to 100%
  10. additiona mixture of acetonitrile/water 10/90 and ammonium acetate (0.1 M, column KR-100-7-C8, 50 mm×250 mm, flow 40 ml/min)
  11. additionThe product containing fractions
  12. customthe acetonitrile was removed by evaporation
  13. additionEtOAc (10 ml) was added
  14. washthe organic phase was washed with two portions of brine
  15. dry with materialdried (MgSO4)

出典と根拠

ORDレコード
ord-e91e493b34184eff84399fbee6bd1717
出典データセット
uspto-grants-2009_04
特許番号
US07521461B2

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