Water → HCID 68565476, 화합물

HRID 1593544노트

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HRID 1593544 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

HCID 68565476HCID 68565476, 화합물수율 98.9%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 6228Dimethylformamide용매

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온도
45 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a39f231c7467404392cb916e37e21d85
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07297715B2

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