Water → HCID 178519580, compound

HRID 1419657Notes

Reaction equation

HRID 1419657 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C@H:11]3[CH2:16][CH2:15][C@H:14]([C:17]4[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[C:19]([F:26])[CH:18]=4)[CH2:13][CH2:12]3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.S(=O)(=O)(O)O>CCOCC>[O:1]1[C:5]2([CH2:6][CH2:7][CH:8]([C@H:11]3[CH2:12][CH2:13][C@H:14]([C:17]4[CH:25]=[CH:24][C:20]([CH2:21][OH:22])=[C:19]([F:26])[CH:18]=4)[CH2:15][CH2:16]3)[CH2:9][CH2:10]2)[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 21226445Aluminium lithium hydrideHCID 178524366HCID 178524366, compound

Product 1

HCID 178519580HCID 178519580, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

5.7 g of 4-[trans-4-(1,4-dioxaspiro[4,5]dec-8-yl)cyclohexyl]-2-fluorobenzoic acid were added to a suspension of 3 g of lithium aluminium hydride in 100 ml of dry ether and, after stirring under reflux for 23 hrs., cooled to 0° C., treated cautiously with 25 ml of water and then 100 ml of 3N sulfuric acid. The reaction mixture was thereupon extracted with ether, the organic phase was dried over sodium sulfate, filtered and the filtrate was evaporated. Chromatography of the residue on silica gel with methylene chloride/acetone (95:5) gave 3.1 g of 4-[trans-4-(1,4-dioxaspiro[4,5]dec-8-yl)cyclohexyl]-2-fluorobenzyl alcohol as colorless crystals.

Workup

  1. temperatureunder reflux for 23 hrs
  2. extractionThe reaction mixture was thereupon extracted with ether
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-4025c354d8204182a1acfc0b55854def
Source dataset
uspto-grants-1999_03
Patent number
US05888423

Reaction notes

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