Dichloromethane → 3,3-Bis-(3-methylthiophen-2-yl)-prop-2-en-1-ol

HRID 1247684노트

반응식

HRID 1247684 반응식
C([O:3][C:4](=O)[CH:5]=[C:6]([C:13]1[S:14][CH:15]=[CH:16][C:17]=1[CH3:18])[C:7]1[S:8][CH:9]=[CH:10][C:11]=1[CH3:12])C.CC(C[AlH]CC(C)C)C.[Cl-].[NH4+].C(Cl)Cl>C1COCC1>[CH3:12][C:11]1[CH:10]=[CH:9][S:8][C:7]=1[C:6]([C:13]1[S:14][CH:15]=[CH:16][C:17]=1[CH3:18])=[CH:5][CH2:4][OH:3]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 685759983,3-Bis-(3-methyl-thiophen-2-yl)-acrylic acid ethyl ester

생성물 1

HCID 219076783,3-Bis-(3-methylthiophen-2-yl)-prop-2-en-1-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3,3-bis-(3-methyl-thiophen-2-yl)-acrylic acid ethyl ester (2.12 g, 7.27 mmol) in THF (20 ml) was added a solution of DIBAL-H (1.5 M in toluene, 33 ml, 49.5 mmol) at −20° C. The reaction mixture was stirred for a further 2 h. A solution of ammonium chloride was added followed by methylene chloride (150 ml) and decalite. The mixture was filtered and the filter was washed with additional methylene chloride (500 ml). The combined organic phases were evaporated to give crude product. Purification on column chromatography gave 3,3-bis-(3-methyl-thiophen-2-yl)-prop-2-en-1-ol in 376 mg (21%) yield.

후처리

  1. filtrationThe mixture was filtered
  2. washthe filter was washed with additional methylene chloride (500 ml)
  3. customThe combined organic phases were evaporated
  4. customto give crude product
  5. customPurification on column chromatography

출처 및 근거

ORD 기록
ord-f597600d2491423e94ca3ce1f26f2e74
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129268B2

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