Hydrochloric Acid → 1-(Bicyclo[2.2.1]hept-5-en-2-yl)-2,2,4,4,4-pentafluorobutane-1,3,3-triol

HRID 1869116노트

반응식

HRID 1869116 반응식
C([Li])CCC.[F:6][C:7]([F:15])([F:14])[CH:8]([OH:13])[C:9]([F:12])(F)[F:10].[CH:16]12[CH2:22][CH:19]([CH:20]=[CH:21]1)[CH2:18][CH:17]2[CH:23]=[O:24].Cl.[O:26]1CCCC1>CCCCCC>[CH:16]12[CH2:22][CH:19]([CH:20]=[CH:21]1)[CH2:18][CH:17]2[CH:23]([OH:24])[C:9]([F:12])([F:10])[C:8]([OH:26])([OH:13])[C:7]([F:15])([F:14])[F:6]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 135291,1,1,3,3,3-Hexafluoro-2-propanolHCID 95117Bicyclo(2.2.1)hept-5-ene-2-carboxaldehydeHCID 178418339Butyllithium

생성물 1

HCID 222370731-(Bicyclo[2.2.1]hept-5-en-2-yl)-2,2,4,4,4-pentafluorobutane-1,3,3-triol수율 80%

시약·촉매·용매 1

HCID 8058Hexane용매

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온도
0 °C

실험 절차

In a nitrogen atmosphere at −70° C., 1290 ml of 1.6M n-butyllithium in hexane was added to a mixture of 168 g of 1,1,1,3,3,3-hexafluoro-2-propanol and 1200 g of tetrahydrofuran. The mixture was allowed to warm up slowly to 0° C. and stirred at the temperature for 30 minutes. Then 134 g of 5-norbornene-2-carboxaldehyde was added at 0° C. The mixture was stirred for 1 hour, after which dilute hydrochloric acid was added for quenching and neutralization. This was followed by conventional aqueous work-up and purification by silica gel column chromatography, collecting 230 g of 1-(5-norbornen-2-yl)-2,2,4,4,4-pentafluorobutane-1,3,3-triol (yield 80% based on the 1,1,1,3,3,3-hexafluoro-2-propanol).

후처리

  1. stirringThe mixture was stirred for 1 hour
  2. customfor quenching
  3. customThis was followed by conventional aqueous work-up and purification by silica gel column chromatography
  4. customcollecting 230 g of 1-(5-norbornen-2-yl)-2,2,4,4,4-pentafluorobutane-1,3,3-triol (yield 80%

출처 및 근거

ORD 기록
ord-7865aa7ca71b4e469ec7648ef55f5df5
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07638256B2

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