Hydrochloric Acid → HCID 57130819, compound

HRID 1490137Notes

Reaction equation

HRID 1490137 reaction equation
[O:1]([C@H:8]1[CH2:12][CH2:11][C@H:10]([O:13]C2CCCCO2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO>[O:1]([C@H:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 56974686HCID 56974686, compound

Product 1

HCID 57130819HCID 57130819, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (1S,3S)-1-phenoxy-3-tetrahydropyranyloxycyclopentane (2.16 g, 8.20 mmol) in methanol (50 ml) was added 6N aqueous hydrochloric acid (5 ml) and the mixture stirred for 2 h at room temperature. Volatiles were removed under reduced pressure and chromatographic purification of the residue {SiO2, 150 g; hexane/ethyl acetate (3:1 )} provided 1.33 g (91%) of the title compound as a colorless oil: 1H NMR δ7.35-7.20 (m, 2H), 6.98-6.82 (m, 3H), 4.97-4.88 (m, 1H), 4.60-4.50 (m, 1H), 2.32-2.01 (m, 4H), 1.97-1.83 (m, 1H), 1.75-1.40 (m, 2H).

Workup

  1. customVolatiles were removed under reduced pressure and chromatographic purification of the residue {SiO2, 150 g

Sources & evidence

ORD record
ord-3d5c8300726f4177b9dda9ebce0b1150
Source dataset
uspto-grants-1997_10
Patent number
US05681858

Reaction notes

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