1(5-Methyl-thien-2-yl) 3,4-dihydro-4,4-dimethyl-7-naphthaldehyde → Ethyl 4-[1-(2,2-dimethoxyethyl)-2-{1-(5-methyl-thien-2-yl)3,4-dihydro-4,4-dimethyl-naphthalen-7-yl}-(E)-ethen-1-yl]-benzoate

HRID 1375265

반응식

HRID 1375265 반응식
C(OP([C:9]([O:25][CH3:26])([O:23][CH3:24])[CH2:10][CH2:11][C:12]1[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=1)(OCC)=O)C.[Li]CCCC.[CH3:32][C:33]1[S:37][C:36]([C:38]2[C:47]3[C:42](=[CH:43][CH:44]=[C:45]([CH:48]=O)[CH:46]=3)[C:41]([CH3:51])([CH3:50])[CH2:40][CH:39]=2)=[CH:35][CH:34]=1.CC1SC(C2C3C(=CC=C(C=O)C=3)C(CC)(CC)CC=2)=CC=1>C1COCC1.CCOCC>[CH3:26][O:25][CH:9]([O:23][CH3:24])[CH2:10]/[C:11](/[C:12]1[CH:13]=[CH:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:21][CH:22]=1)=[CH:48]\[C:45]1[CH:46]=[C:47]2[C:42]([C:41]([CH3:51])([CH3:50])[CH2:40][CH:39]=[C:38]2[C:36]2[S:37][C:33]([CH3:32])=[CH:34][CH:35]=2)=[CH:43][CH:44]=1

참가 물질

7

반응물 4

HCID 186200661(5-Methyl-thien-2-yl) 3,4-dihydro-4,4-dimethyl-7-naphthaldehydeHCID 210795151(5-Methyl-thien-2-yl)3,4-dihydro-4,4-diethyl-7-naphthaldehydeHCID 57037360Ethyl 4-(diethoxyphosphoryl-3,3-dimethoxypropyl)benzoate2회HCID 178418339Butyllithium

생성물 1

HCID 22883504Ethyl 4-[1-(2,2-dimethoxyethyl)-2-{1-(5-methyl-thien-2-yl)3,4-dihydro-4,4-dimethyl-naphthalen-7-yl}-(E)-ethen-1-yl]-benzoate수율 90%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-10 °C

실험 절차

To a cold (−78° C.) solution of ethyl 4-(diethoxyphosphoryl-3,3-dimethoxypropyl)benzoate (Compound D, 1.4 g, 3.6 mmol), in THF (20 mL) was added n-BuLi (1.6 M solution in hexane, 2.5 ml, 4 mmol). The mixture was stirred for 20 minutes at −78° C. and 10 min. at −10° C. The reaction mixture was recooled to −78° C. and 1(5-methyl-thien-2-yl)3,4-dihydro-4,4-dimethyl-7-naphthaldehyde (Compound G, 650 mg, 2.3 mmol) in THF (4 mL) was added to it. The mixture was stirred for 2 hours at −10° C. and diluted with ether (100 mL), washed with brine (10 mL) dried with MgSO4 and the solvent was removed by distillation to to afford a cis and trans (E and Z) isomeric mixture. Purification by chromatography on silica gel of the crude material afforded the title compound as an oil (˜90% purity).

후처리

  1. customwas recooled to −78° C.
  2. stirringThe mixture was stirred for 2 hours at −10° C.
  3. washwashed with brine (10 mL)
  4. dry with materialdried with MgSO4
  5. customthe solvent was removed by distillation
  6. customto to afford a cis and trans (E and Z) isomeric mixture
  7. customPurification by chromatography on silica gel of the crude material

출처 및 근거

ORD 기록
ord-aa329f9e75124c4ab24450bea0d74863
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07166726B2

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