Hydrochloric Acid → HCID 11231086, compound

HRID 1744038Notes

Reaction equation

HRID 1744038 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[OH:11][CH:12]([CH:22]1[CH2:27][CH:26]2[CH2:28][CH:23]1[CH:24]=[CH:25]2)[C:13]([F:21])([F:20])[C:14](=[O:19])[C:15]([F:18])([F:17])[F:16].Cl>C1(C)C=CC=CC=1>[CH:23]12[CH2:28][CH:26]([CH:25]=[CH:24]1)[CH2:27][CH:22]2[CH:12]([OH:11])[C:13]([F:20])([F:21])[CH:14]([OH:19])[C:15]([F:18])([F:17])[F:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 22237068HCID 22237068, compound

Product 1

HCID 11231086HCID 11231086, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

210 mL of diisobutylaluminum hydride (1.0M toluene solution) was added under nitrogen atmosphere at 0° C. to the mixture of 27.0 g of 1-hydroxy-1-(5-norbornene-2-yl)-2,2,4,4,4-pentafluorobutane-3-one (synthesized according to [Example 1]) and 50 g of toluene, then the solution was stirred for 10 hours at 20° C. Dilute hydrochloric acid was added to quench the reaction and to neutralize it, and then the standard aqueous work-up was performed. The product was purified by silica gel column chromatography to yield 25.9 g of 1-(5-norbornene-2-yl)-2,2,4,4,4-pentafluorobutane-1,3-diol (yield was 95%).

Workup

  1. customto quench
  2. customthe reaction
  3. customThe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-20306e808f304cd2961885b9a1b730db
Source dataset
uspto-grants-2006_03
Patent number
US07012161B2

Reaction notes

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