Ethyl Acetate → 1,3-Diphenoxy-2-((methoxy)methoxy)propane

HRID 847607Notes

Reaction equation

HRID 847607 reaction equation
C1(CCC(O)CCC2C=CC=CC=2)C=CC=CC=1.[O:19]([CH2:26][CH:27]([OH:36])[CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:37]([O:40][CH2:41]C)(=O)C>CCCCCC>[O:19]([CH2:26][CH:27]([O:36][CH2:37][O:40][CH3:41])[CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 121401,3-Diphenoxy-2-propanolHCID 128385101,5-Diphenylpentan-3-ol

Product 1

HCID 229101291,3-Diphenoxy-2-((methoxy)methoxy)propane

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Using the procedure of Example 51 but replacing 1,5-diphenyl-3-pentanol with the resultant compound of Example 4 gave, after silica gel chromatography using 10% ethyl acetate in hexane, 80 mg (49%) of the desired compound (Rf 0.42, 20% ethyl acetate in hexane). 1H NMR (CDCl3) δ 3 44 (s, 3H), 4.18 (dd, J=10, 6 Hz, 2H), 4.22 (dd, J=15, 6 Hz, 2H), 4.33 (pentet, J=6 Hz, 1H), 4.85 (s, 2H), 6.9-7.0 (m, 6H), 7.25-7.35 (m, 4H). Mass spectrum (M+NH4)+ =306.

Workup

  1. customgave

Sources & evidence

ORD record
ord-9354963358f4443f9d02c43b54446b83
Source dataset
uspto-grants-1992_08
Patent number
US05142056

Reaction notes

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