Methanesulfonic acid, trifluoro-, 3,4-dihydro-1-naphthalenyl ester → 4-(3,4-Dihydro-naphthalen-1-yl)-benzoic acid ethyl ester

HRID 1793989Notes

Reaction equation

HRID 1793989 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([Sn](CCCC)(CCCC)CCCC)=[CH:7][CH:6]=1)[CH3:2].FC(F)(F)S(O[C:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:34][CH2:33][CH:32]=1)(=O)=O>>[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:6]=[CH:7][C:8]([C:34]2[C:35]3[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:31][CH2:32][CH:33]=2)=[CH:9][CH:10]=1)[CH3:2]

Participants

3

Reactant 2

HCID 10967830Methanesulfonic acid, trifluoro-, 3,4-dihydro-1-naphthalenyl esterHCID 11235991Ethyl 4-(tributylstannyl)benzoate

Product 1

HCID 696525924-(3,4-Dihydro-naphthalen-1-yl)-benzoic acid ethyl esterYield 93.5%

Procedure

4-(Tri-n-butyl-stannyl)-benzoic acid ethyl ester of Example 15, Step A (2.58 g, 5.88 mmol) and 3,4-dihydro-naphthalen-1-yl trifluoromethanesulfonate (1.80 g, 6.47 mmol) were reacted in the manner of Example 15, Step B. Purification by flash column chromatography on silica gel, eluting with a solvent gradient of from 0 to 10% ethyl acetate in hexane followed by recrystallization from pentane (−20° C.) afforded the title compound (1.53 g) as slightly yellow crystals, m.p. 81° C.

Workup

  1. customPurification by flash column chromatography on silica gel
  2. washeluting with a solvent gradient of from 0 to 10% ethyl acetate in hexane
  3. customfollowed by recrystallization from pentane (−20° C.)

Sources & evidence

ORD record
ord-05862c710ec44e378ce4f99855eb0306
Source dataset
uspto-grants-2006_04
Patent number
US07022699B2

Reaction notes

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