5-{4-[(Phenylmethyl)oxy]-1-buten-1-yl]-3,6-dihydro-2H-pyran → 4-(Tetrahydro-2H-pyran-3-yl)-1-butanol

HRID 1011041Notes

Reaction equation

HRID 1011041 reaction equation
C1(C[O:8][CH2:9][CH2:10][CH:11]=[CH:12][C:13]2[CH2:18][O:17][CH2:16][CH2:15][CH:14]=2)C=CC=CC=1.[H][H]>[Pd].C(OCC)(=O)C>[O:17]1[CH2:16][CH2:15][CH2:14][CH:13]([CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[CH2:18]1

Participants

5

Reactant 2

HCID 673137985-{4-[(Phenylmethyl)oxy]-1-buten-1-yl]-3,6-dihydro-2H-pyranHCID 178418361HCID 178418361, compound2×

Product 1

HCID 576997684-(Tetrahydro-2H-pyran-3-yl)-1-butanolYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-{4-[(phenylmethyl)oxy]-1-buten-1-yl}-3,6-dihydro-2H-pyran (2.03 g) and 10% palladium on carbon (88 mg) in ethyl acetate (83 ml) was hydrogenated at atmospheric pressure and room temperature. Hydrogen uptake (˜500 ml) was complete after 15 hours. The catalyst was filtered through celite and the filtrate concentrated in vacuo to afford a colourless oil. Analysis by 1H-NMR showed that the benzyl group was present in the majority of the compound. Hydrogenation was continued under the same conditions for a further 24 hours with additional hydrogen uptake of ˜300 ml. The catalyst was filtered through celite and the filtrate concentrated in vacuo to afford the title compound as a colourless oil (1.21 g).

Workup

  1. customwas hydrogenated at atmospheric pressure and room temperature
  2. filtrationThe catalyst was filtered through celite
  3. concentrationthe filtrate concentrated in vacuo
  4. customto afford a colourless oil
  5. filtrationThe catalyst was filtered through celite
  6. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-26dd2917c76b40178716b9b82e2e143b
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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