Water → HCID 68565476、化合物

HRID 1593544ノート

反応式

HRID 1593544 の反応式
[OH:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]([CH3:14])([CH2:12][CH3:13])[C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:24][CH2:25][CH2:26][O:27]CC1C=CC=CC=1.O>CN(C=O)C.CO.[Pd]>[OH:27][CH2:26][CH2:25][CH2:24][O:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]([CH3:14])([CH2:12][CH3:13])[C:8]([O:10][CH3:11])=[O:9])=[CH:15][CH:16]=1

参加物

8

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 2776064Benzyl 3-Bromopropyl EtherHCID 21111741Methyl 2-(4-hydroxyphenoxy)-2-methylbutanoate

生成物 1

HCID 68565476HCID 68565476、化合物収率 98.9%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
45 °C

実験手順

To a solution of methyl 2-(4-hydroxyphenoxy)-2-methylbutanoate (5 g, 22.32 mmol) in 30 mL DMF was added cesium carbonate (8.7 g, 26.7 mmol) followed by benzyl 3-bromopropyl ether (7.7 g, 33.6 mmol). The solution was stirred at 45° C. for 24 hr, cooled and poured over water. Extraction with AcOEt followed by washing the extracts with water, drying over anhydrous Na2SO4 and concentrating under reduced pressure gave the crude residue. Purification over silica gel using AcOEt/hexanes furnished the desired alkylated derivative (8.25 g). This product was taken up in MeOH (75 mL) and hydrogenated over 10% Pd/C at 40 psi to provide methyl 2-(4-(3-hydroxypropoxy)phenoxy)-2-methylbutanoate (6.23 g, quantitative).

後処理

  1. temperaturecooled
  2. extractionExtraction with AcOEt
  3. washby washing the extracts with water
  4. dry with materialdrying over anhydrous Na2SO4
  5. concentrationconcentrating under reduced pressure
  6. customgave the crude residue
  7. customPurification over silica gel
  8. customfurnished the desired alkylated derivative (8.25 g)

出典と根拠

ORDレコード
ord-a39f231c7467404392cb916e37e21d85
出典データセット
uspto-grants-2007_11
特許番号
US07297715B2

反応ノート

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