Aluminium lithium hydride → 2-(2-Nonadecynyl)-1,3-propanediol

HRID 1885461노트

반응식

HRID 1885461 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([CH:26]([C:32](OCC)=[O:33])[C:27](OCC)=[O:28])#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>CCOCC>[CH2:7]([CH:26]([CH2:27][OH:28])[CH2:32][OH:33])[C:8]#[C:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 856665962-Nonadecynylpropanedioic acid, diethyl ester

생성물 1

HCID 197643602-(2-Nonadecynyl)-1,3-propanediol수율 56.5%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

A mixture of 1.8 g of lithium aluminum hydride in 150 ml of ether is prepared at 0° C. To this is added a solution of 11.7 g of 2-nonadecynylpropanedioic acid, diethyl ester in ether. This mixture is refluxed for 4 hours then the reaction is quenched with aqueous sodium sulfate. After stirring for 2 days, the reaction is diluted with ethyl acetate and filtered. The residue is treated with methanol, 1N sodium hydroxide and tetrahydrofuran and then evaporated. The residue is dissolved in ether and washed with brine and purified by flash chromatography, (4:6 ethyl acetate:petroleum ether), to give 5.3 g of the desired product as white plates, mp. 55° C.

후처리

  1. customis prepared at 0° C
  2. temperatureThis mixture is refluxed for 4 hours
  3. customthe reaction is quenched with aqueous sodium sulfate
  4. additionthe reaction is diluted with ethyl acetate
  5. filtrationfiltered
  6. additionThe residue is treated with methanol, 1N sodium hydroxide and tetrahydrofuran
  7. customevaporated
  8. dissolutionThe residue is dissolved in ether
  9. washwashed with brine
  10. custompurified by flash chromatography, (4:6 ethyl acetate:petroleum ether),

출처 및 근거

ORD 기록
ord-7ee34da4dd76460d80087f5f08feedb8
출처 데이터셋
uspto-grants-1992_09
특허 번호
US05144045

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