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

HRID 1247684ノート

反応式

HRID 1247684 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f597600d2491423e94ca3ce1f26f2e74
出典データセット
uspto-grants-2006_10
特許番号
US07129268B2

反応ノート

読み込み中…