1-Octyne → HCID 13588520, 화합물

HRID 1284439노트

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HRID 1284439 반응식
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]

참가 물질

10

반응물 5

HCID 123701-OctyneHCID 779706-Bromo-1-hexanolHCID 263182Tetrahydropyranyl ether2회HCID 35630467-tetradecyn-1-olHCID 178418339Butyllithium

생성물 1

HCID 13588520HCID 13588520, 화합물

시약·촉매·용매 4

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매HCID 12679Hexamethylphosphoramide용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-67481f5b33984f97a48a7964aecd40c6
출처 데이터셋
uspto-grants-1986_01
특허 번호
US04563348

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