Tetrahydrofuran → trans-3-[3-(1-Dodecynyl)phenyl]propen-1-ol

HRID 440410ノート

反応式

HRID 440410 の反応式
[C:1]([C:13]1[CH:14]=[C:15](/[CH:19]=[CH:20]/[C:21](OCC)=[O:22])[CH:16]=[CH:17][CH:18]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].O1CCCC1.[H-].C([Al+]CC(C)C)C(C)C.[OH-].[Na+]>C(OCC)(=O)C>[C:1]([C:13]1[CH:14]=[C:15]([CH2:19]/[CH:20]=[CH:21]/[OH:22])[CH:16]=[CH:17][CH:18]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 14798Sodium Hydroxide2 回HCID 18373045Ethyl trans-3-[3-(1-Dodecynyl)phenyl]-2-propenoateHCID 21225700Diisobutylaluminumhydride

生成物 1

HCID 18372907trans-3-[3-(1-Dodecynyl)phenyl]propen-1-ol収率 81.5%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

To a solution of ethyl trans-3-[3-(1-dodecynyl)phenyl]-2-propenoate (10.0 g) and dry tetrahydrofuran (100 ml) at -78° C. was added diisobutylaluminum hydride (1.5M in toluene) (49 ml) slowly. The reaction mixture was stirred for 20 mins at -78° C., and 25% sodium hydroxide solution (3 ml) was added. The mixture was slowly warmed to room temperature and an additional 25% sodium hydroxide solution (3 ml) was added. The mixture was diluted with ethyl acetate and washed with water and brine. The organic phase was separated, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was flash chromatographed over silica gel (eluted with ethyl acetate/hexane/1:3). The appropriate fractions were collected and evaporated to afford 7.14 g (81%) of product.

後処理

  1. temperatureThe mixture was slowly warmed to room temperature
  2. washwashed with water and brine
  3. customThe organic phase was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customchromatographed over silica gel (eluted with ethyl acetate/hexane/1:3)
  8. customThe appropriate fractions were collected
  9. customevaporated

出典と根拠

ORDレコード
ord-67649b2143eb4abd81fd007817dbe983
出典データセット
uspto-grants-1996_05
特許番号
US05519062

反応ノート

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