Reaction #50594

ord-839f4529654e48c7bbcee0290e2694f8

Reaction equation

O=C([O-])/C=C/C(=O)[O-]
Fumarate
CC(C)Oc1cc2ccc(=O)oc2cc1OCCCOS(C)(=O)=O
7-[3-(methanesulfonyloxy)propoxy]-6-(1-methylethoxy)-2H-1-benzopyran-2-one
c1ccc(C2CCNCC2)cc1
4-phenylpiperidine
COC(C)(C)C
TBME
→
CC(C)Oc1cc2ccc(=O)oc2cc1OCCCN1CCC(c2ccccc2)CC1
6-(1-methylethoxy)-7-[3-(4-phenyl-1-piperidinyl)propoxy]-2H-1-benzopyran-2-one
Yield 69.0%

Reactants

O=C([O-])/C=C/C(=O)[O-]
Fumarate
CC(C)Oc1cc2ccc(=O)oc2cc1OCCCOS(C)(=O)=O
7-[3-(methanesulfonyloxy)propoxy]-6-(1-methylethoxy)-2H-1-benzopyran-2-one
c1ccc(C2CCNCC2)cc1
4-phenylpiperidine
COC(C)(C)C
TBME

Reagents

None

Solvents

CC(C)=O
acetone
CCO
ethanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherMethod B (24 h at 60° C.)

Procedure

Method B (24 h at 60° C.); starting materials: 7-[3-(methanesulfonyloxy)propoxy]-6-(1-methylethoxy)-2H-1-benzopyran-2-one (example 73) and 4-phenylpiperidine; yield 69%; fusion point 86°-87° C. (from TBME). Fumarate: method E; yield 90%; fusion point 164°-167° C. (from ethanol and acetone).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05428038uspto-grants-1995_06