Tetrahydrofuran → HCID 20358499, compound

HRID 2083402Notes

Reaction equation

HRID 2083402 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][C:11]([CH2:15][C:16](CC3(C)COC(C4C=CC(F)=CC=4)OC3)=O)([CH3:14])[CH2:10][O:9]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:39]1CCCC1>CCOCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][C:11]([CH3:14])([CH:15]([CH3:16])[OH:39])[CH2:10][O:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 54352404HCID 54352404, compound

Product 1

HCID 20358499HCID 20358499, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2-(p-Fluorophenyl)-5-methyl-1,3-dioxan-5-yl-methyl ketone (11.85 g) in dry ether (100 ml) was added to a slurry of lithium aluminium hydride (2.5 g) in dry ether (50 ml) and the mixture was heated under reflux for 4 hours. Moist tetrahydrofuran (20 ml) was added and the mixture was filtered. The filtrate was concentrated and the crude product was recrystallised from ethyl acetate/light petroleum (b.p. 60°-80°) as white crystals, m.p.78°, of the pure cis isomer.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. filtrationthe mixture was filtered
  4. concentrationThe filtrate was concentrated
  5. customthe crude product was recrystallised from ethyl acetate/light petroleum (b.p. 60°-80°) as white crystals, m.p.78°, of the pure cis isomer

Sources & evidence

ORD record
ord-7198e608b807463db5d54bf2d6619bee
Source dataset
uspto-grants-1978_04
Patent number
US04085222

Reaction notes

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