Sulfuric Acid → 6,6-Dimethylhept-1-en-4-yn-3-ol

HRID 413983ノート

反応式

HRID 413983 の反応式
C([Li])CCC.CCCCCC.[C:12]([C:16]#[CH:17])([CH3:15])([CH3:14])[CH3:13].[CH:18]([CH:20]=[CH2:21])=[O:19].[Cl-].[NH4+].S(=O)(=O)(O)O>O1CCCC1>[CH3:13][C:12]([CH3:15])([CH3:14])[C:16]#[C:17][CH:18]([OH:19])[CH:20]=[CH2:21]

参加物

8

反応物 6

HCID 1118Sulfuric AcidHCID 7847AcroleinHCID 8058HexaneHCID 135123,3-Dimethyl-1-butyneHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

生成物 1

HCID 109755616,6-Dimethylhept-1-en-4-yn-3-ol収率 60.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

Butyllithium 1.6 M solution in hexane (106.2 ml, 0.17 mole) was added dropwise during 70 minutes to a mixture of t-butylacetylene (13.3 gr., 0.162 mole) and tetrahydrofuran (133.1 ml) at 0° C. A solution of freshly distilled acrolein (10 gr., 0.17 mole) in tetrahydrofuran (26.6 ml) was added to the reaction mixture at 0° C. during 45 minutes. The reaction mixture was stirred at 0° C. for 40 minutes. It was further stirred for 18 hours at room temperature. Saturated ammonium chloride solution (45 ml) was added. The reaction mixture was brought to pH 6 using 10% sulfuric acid (about 85 ml). Tetrahydrofuran was evaporated under reduced pressure. The residue was extracted by dichloromethane. The organic phase was washed with water and dried. The dichloromehane was removed to give the crude product (20.1 gr., 90% yield). Pure 6,6-dimethylhept-1-en-4-yn-3-ol was obtained by distillation. Boiling point was 83° C. at 24 mbar. 13.5 gr. were obtained (60.6% yield).

後処理

  1. stirringIt was further stirred for 18 hours at room temperature
  2. customTetrahydrofuran was evaporated under reduced pressure
  3. extractionThe residue was extracted by dichloromethane
  4. washThe organic phase was washed with water
  5. customdried
  6. customThe dichloromehane was removed
  7. customto give the crude product (20.1 gr., 90% yield)

出典と根拠

ORDレコード
ord-945bfefdebd44d67b83ee97c8f37fc92
出典データセット
uspto-grants-2003_05
特許番号
US06570044B2

反応ノート

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