1-Octyne → HCID 13588520、化合物

HRID 1284439ノート

反応式

HRID 1284439 の反応式
O1CC[CH2:4][CH2:3][CH:2]1[O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1.[CH2:14](O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]#[C:21][CH2:22]CCCCC.[CH:29]#CCCCCCC.C([Li])CCC.C(Br)CCCCCO>O1CCCC1.CCCCCC.CN(C)P(=O)(N(C)C)N(C)C.O>[C:8]([O:7][CH:2]([CH2:3][CH3:4])[CH3:29])(=[O:9])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:14]/[CH:15]=[CH:16]\[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

参加物

10

反応物 5

HCID 123701-OctyneHCID 779706-Bromo-1-hexanolHCID 263182Tetrahydropyranyl ether2 回HCID 35630467-tetradecyn-1-olHCID 178418339Butyllithium

生成物 1

HCID 13588520HCID 13588520、化合物

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒HCID 12679Hexamethylphosphoramide溶媒

反応条件

温度
0 °C

実験手順

Tetrahydropyranyl ether derivative of 7-tetradecyne-1-ol. To a cooled solution (-15° C.) of 1-octyne (7.95 g) in 30 ml of dry tetrahydrofuran under a nitrogen atmosphere was added dropwise 30.4 ml of 2.09M butyllithium in hexane. The addition took 30 minutes, after which the reaction was warmed to 0° C. and then cooled to -10° C. This solution was added slowly to a cold (0° C.) solution of the tetrahydropyranyl ether derivative of hexamethylene bromohydrin (14.80 g) in 50 ml of hexamethylphosphoric triamide under nitrogen. The reaction mixture was allowed to warm to room temperature, stirred overnight, poured into cold water, and extracted three times with hexane. The combined organic layers were washed with water (three times) and brine, and dried with anhydrous Na2SO4. Removal of solvent under reduced pressure yielded 18.55 g of impure tetrahydropyranyl ether derivative of 7-tetradecyne-1-ol as a yellow oil. This material was used without further purification in the next step.

後処理

  1. additionThe addition
  2. temperaturecooled to -10° C
  3. temperatureto warm to room temperature
  4. extractionextracted three times with hexane
  5. washThe combined organic layers were washed with water (three times) and brine
  6. dry with materialdried with anhydrous Na2SO4
  7. customRemoval of solvent under reduced pressure

出典と根拠

ORDレコード
ord-67481f5b33984f97a48a7964aecd40c6
出典データセット
uspto-grants-1986_01
特許番号
US04563348

反応ノート

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