Phenol → (1R*,4R*)-4-methoxymethoxy-2-cyclopenten-1-ol

HRID 1199848Notes

Reaction equation

HRID 1199848 reaction equation
C([C:5]([O:7][CH2:8]CC(O)C)=[O:6])(C)(C)C.[C:13]1([OH:19])[CH:18]=[CH:17][CH:16]=[CH:15]C=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:8][O:7][CH2:5][O:6][C@@H:16]1[CH2:15][C@@H:13]([OH:19])[CH:18]=[CH:17]1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 150032733-Hydroxybutyl 2,2-dimethylpropanoate

Product 1

HCID 14804795(1R*,4R*)-4-methoxymethoxy-2-cyclopenten-1-olYield 151.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3.47 g (19.9 mmol) of alcohol 25 (prepared in 30-(1)), 2.81 g (29.9 mmol) of phenol, and 7.88 g (29.9 mmol) of triphenylphosphine in 100 ml of dry THF is added a solution of 4.65 ml of diethyl azodicarboxylate in 40 ml of dry THF dropwise under ice cooling. After additional stirring at the same temperature for 20 minutes, the mixture is stirred for further 2 and half hours. The reaction mixture is concentrated under reduced pressure and the residue is purified by column chromatography on silica gel (200 g of silica gel, ethyl acetate:n-hexane=1:49 to 1:19) to give 4.35 g of the desired phenyl ether 3 as an oil in 87.4% yield.

Workup

  1. stirringthe mixture is stirred for further 2 and half hours
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. customthe residue is purified by column chromatography on silica gel (200 g of silica gel, ethyl acetate:n-hexane=1:49 to 1:19)

Sources & evidence

ORD record
ord-15d68fd7d9994b63a0c25dde523c7d38
Source dataset
uspto-grants-1990_02
Patent number
US04902811

Reaction notes

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