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

HRID 1744036Notes

Reaction equation

HRID 1744036 reaction equation
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>>[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]

Participants

6

Reactant 5

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

Product 1

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

Conditions

Temperature
0 °C

Procedure

1290 mL of butyllithium (1.6 M hexane solution) was added to a mixture of 168 g of 1,1,1,3,3,3-hexafluoro-2-propanol and 1200 g of tetrahydrofuran at −70° C. under a nitrogen atmosphere. The temperature was increased to 0° C. gradually, and stirred at the temperature for 30 minutes. Then, 134 g of 5-norbornene-2-carbaldehyde was added thereto at 0° C. After stirring for 1 hour, dilute hydrochloric acid was added to terminate the reaction and to neutralize it. After the standard aqueous work-up, the product was purified by silica gel column chromatography to yield 230 g of 1-(5-norbornene-2-yl)-2,2,4,4,4-pentafluorobutane-1,3,3-triol (yield from 1,1,1,3,3,3-hexafluoro-2-propanol was 80%)

Workup

  1. customat 0° C
  2. stirringAfter stirring for 1 hour
  3. customto terminate
  4. customthe reaction
  5. customAfter the standard aqueous work-up, the product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-adf7c6181fd449c2b0e524b493c527b7
Source dataset
uspto-grants-2006_03
Patent number
US07012161B2

Reaction notes

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