Hexane → Ethyl 3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)propiolate

HRID 428230

반응식

HRID 428230 반응식
[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:9]([CH3:14])([CH3:13])[CH2:8][CH2:7][C:6]([CH3:16])([CH3:15])[C:5]=2[CH:4]=1)#[CH:2].C([Li])CCC.CCCCCC.[CH2:28]([O:30][C:31](Cl)=[O:32])[CH3:29]>CCOCC>[CH3:13][C:9]1([CH3:14])[CH2:8][CH2:7][C:6]([CH3:16])([CH3:15])[C:5]2[CH:4]=[C:3]([C:1]#[C:2][C:31]([O:30][CH2:28][CH3:29])=[O:32])[CH:12]=[CH:11][C:10]1=2

참가 물질

6

반응물 4

HCID 8058HexaneHCID 10928Ethyl chloroformateHCID 147265491,1,4,4-Tetramethyl-6-ethynyl-1,2,3,4-tetrahydronaphthaleneHCID 178418339Butyllithium

생성물 1

HCID 11000580Ethyl 3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)propiolate

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
-10 °C

실험 절차

To a cold solution (−78° C.) of 2-ethynyl,5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene (900 mgs, 4.3 mmols) in ether (20 ml) was added n-butyllithium in hexane (5.6 mmols). The mixture was stirred for 45 mins, and ethylchloroformate (1.3 g, 12 mmols) was added via syringe. Stirring was continued for 45 mins then the mixture was warmed gradually to −10° C. and quenched by adding sodium bicarbonate (NaHCO3) solution (10 ml). Diethyl ether (100 ml) was added, the organic phase washed with water (10 ml), brine (10 ml), and dried (MgSO4). The solvent was removed in vacuo. Purification of the residue over silicagel (5% ethylacetate in hexane) gave the title compound as a colorless oil.

후처리

  1. stirringStirring
  2. waitwas continued for 45 mins
  3. customquenched
  4. additionby adding sodium bicarbonate (NaHCO3) solution (10 ml)
  5. additionDiethyl ether (100 ml) was added
  6. washthe organic phase washed with water (10 ml), brine (10 ml)
  7. dry with materialdried (MgSO4)
  8. customThe solvent was removed in vacuo
  9. customPurification of the residue over silicagel (5% ethylacetate in hexane)

출처 및 근거

ORD 기록
ord-3e8e7146651c4e688d91778793842f9c
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313163B1

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