Diisopropylamine → 3-(4-Benzyloxyphenyl)2-ethoxy-3-hydroxy-2-methyl propanoic acid ethyl ester

HRID 987285노트

반응식

HRID 987285 반응식
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([O:15][C:16](=[O:22])[CH:17]([O:19][CH2:20][CH3:21])[CH3:18])[CH3:14].[Li+].CC([N-]C(C)C)C.[CH2:31]([O:38][C:39]1[CH:46]=[CH:45][C:42]([CH:43]=[O:44])=[CH:41][CH:40]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:13]([O:15][C:16](=[O:22])[C:17]([O:19][CH2:20][CH3:21])([CH3:18])[CH:43]([C:42]1[CH:41]=[CH:40][C:39]([O:38][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:46][CH:45]=1)[OH:44])[CH3:14]

참가 물질

8

반응물 6

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 247453Ethyl 2-ethoxypropanoateHCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

생성물 1

HCID 542946983-(4-Benzyloxyphenyl)2-ethoxy-3-hydroxy-2-methyl propanoic acid ethyl ester수율 68%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

Di-isopropylamine (1.1 ml; 7.78 mmole) and dry tetrahydrofuran (35 ml) were mixed and cooled to −78° C. under nitrogen athmosphere. n-Butyllithium (1.6 M in hexane, 4.7 ml; 7.52 mmole) was added slowly and the reaction mixture was stirred for 15 minutes. 2-Ethoxypropionic acid ethyl ester was dissolved in a small amount of dry tetrahydrofuran and added slowly to the LDA mixture. The solution was stirred for 30 minutes at low temperature and then 4-benzyloxybenzaldehyde was added followed after 2 minutes by addition of saturated ammonium chloride solution (20 ml). The mixture was warmed to room temperature and the layers were separated. The aqueous phase was extracted twice with ether and the organic phases were combined and washed with hydrochloric acid (0.3 M, 100 ml) and brine dried with magnesium sulfate and evaporated. Purification of the residue by chromatography on silica gel using ethyl acetate: toluene (1:9) with triethylamine (0.1%) as eluant gave 1.63 g (68%) of 3-(4-benzyloxyphenyl)2-ethoxy-3-hydroxy-2-methyl propanoic acid ethyl ester.

후처리

  1. stirringThe solution was stirred for 30 minutes at low temperature
  2. temperatureThe mixture was warmed to room temperature
  3. customthe layers were separated
  4. extractionThe aqueous phase was extracted twice with ether
  5. washwashed with hydrochloric acid (0.3 M, 100 ml) and brine
  6. dry with materialdried with magnesium sulfate
  7. customevaporated
  8. customPurification of the residue by chromatography on silica gel

출처 및 근거

ORD 기록
ord-dc9e0e43e0ab4708aaa28adc30ea6c65
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06630600B1

반응 노트

불러오는 중…