Sodium → Tropenol 4,4'-difluorobenzilate

HRID 2099342Notes

Reaction equation

HRID 2099342 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)([OH:11])[C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=1.[C@@:21]12(O)[N:28](C)[C@@H:25]([CH2:26][CH2:27]1)[CH2:24][CH:23]=[CH:22]2.[Na]>>[F:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)([OH:11])[C:7]([O:9][C@@:10]23[N:28]([CH3:21])[C@@H:25]([CH2:26][CH2:27]2)[CH2:24][CH:23]=[CH:22]3)=[O:8])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 5360545SodiumHCID 12068840Methyl 4,4'-difluorobenzilateHCID 53629842Tropenol

Product 1

HCID 86585677Tropenol 4,4'-difluorobenzilate

Procedure

11.13 g (0.04 mol) of methyl 4,4′-difluorobenzilate 3d and 5.57 g (0.04 mol) of tropenol are reacted with 0.09 g sodium analogously to Example 3, step 3.2. The product is recrystallized from acetonitrile. Yield: 10.43 g (62% of theory); melting point: 233-235° C.

Workup

  1. customThe product is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-f6244f2c56e44d249ec5cf77bc94d588
Source dataset
uspto-grants-2009_08
Patent number
US07569581B2

Reaction notes

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