Acetic Acid → HCID 13883260, compound

HRID 1608265Notes

Reaction equation

HRID 1608265 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][C:7]2[CH2:11][C:10]([CH2:14][OH:15])([CH2:12][OH:13])ON=2)=[CH:4][CH:3]=1.C(O)(=O)C.O>O1CCCC1.O.[Pt](=O)=O>[OH:13][CH2:12][C:10]1[CH:11]=[C:7]([CH2:6][C:5]2[CH:16]=[CH:17][C:2]([F:1])=[CH:3][CH:4]=2)[O:15][CH:14]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 13883256HCID 13883256, compound

Product 1

HCID 13883260HCID 13883260, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 11139377Platinum dioxide monohydrateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

67.9 g of 3-(p-fluorobenzyl)-5,5-bis-(hydroxymethyl)-isoxazoline are taken up in 400 ml of tetrahydrofuran, 80 ml of glacial acetic acid and 40 ml of water, and 1.5 g of platinum(IV) oxide hydrate are added. Hydrogenation is carried out for 5-6 hours at 25°-30° C., a slightly exothermic reaction taking place (cooling). When the absorption of hydrogen is complete, the catalyst is filtered off, the filtrate is evaporated down and the residue is stirred in 400 ml of methylene chloride with 400 ml of 10% strength hydrochloric acid for 1 hour at room temperature. The organic phase is separated off, washed neutral, dried over sodium sulfate and evaporated down. Purification by column chromatography over silica gel with toluene/acetone 9/1 as the eluent gives 37 g of 3-hydroxymethyl-5-(p-fluorobenzyl)-furan of melting point 45°-47° C. ##STR13##

Workup

  1. customa slightly exothermic reaction
  2. temperatureplace (cooling)
  3. customWhen the absorption of hydrogen
  4. filtrationthe catalyst is filtered off
  5. customthe filtrate is evaporated down
  6. customThe organic phase is separated off
  7. washwashed neutral
  8. dry with materialdried over sodium sulfate
  9. customevaporated down
  10. customPurification by column chromatography over silica gel with toluene/acetone 9/1 as the eluent

Sources & evidence

ORD record
ord-15957dafab764f0ba1224c1966039915
Source dataset
uspto-grants-1989_09
Patent number
US04870100

Reaction notes

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