HCID 67485532, compound → HCID 60145978, compound

HRID 2233362Notes

Reaction equation

HRID 2233362 reaction equation
C([O:5][C:6](=[O:20])[CH2:7]/[C:8](/[C:16]([O:18][CH3:19])=[O:17])=[CH:9]\[C:10]1[O:11][C:12]([CH3:15])=[CH:13][CH:14]=1)(C)(C)C>FC(F)(F)C(O)=O.O.C1(C)C=CC=CC=1>[CH3:19][O:18][C:16](/[C:8](=[CH:9]/[C:10]1[O:11][C:12]([CH3:15])=[CH:13][CH:14]=1)/[CH2:7][C:6]([OH:20])=[O:5])=[O:17]

Participants

4

Reactant 1

HCID 67485532HCID 67485532, compound

Product 1

HCID 60145978HCID 60145978, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 22392675Trifluoroacetic acid waterSolvent

Procedure

A solution of E-3-methoxycarbonyl-4-(5-methylfur-2-yl)-but-3-enoic acid t-butyl ester (Method 16; 1.39 g, 4.96 mmol) in trifluoroacetic acid/water (20 ml of 90:10 v/v) was stirred at ambient temperature for 20 mins; the reaction mixture was then diluted with toluene (30 ml) and evaporated in vacuo to yield a brown oil. After further azeotroping with toluene (30 ml), this set solid; trituration with isohexane and collection of the residue yielded the title compound as a brown solid (1.05 g, 95%). NMR 2.33 (s, 3H), 3.65 (s, 2H), 3.72 (s, 3H), 6.29 (d, 1H), 6.85 (d, 1H), 7.41 (s, 1H), 12.34 (bs, 1H).

Workup

  1. customevaporated in vacuo
  2. customto yield a brown oil
  3. customAfter further azeotroping with toluene (30 ml)
  4. customtrituration with isohexane and collection of the residue

Sources & evidence

ORD record
ord-c95c33cd12414197a1ac1d614c24897e
Source dataset
uspto-grants-2010_05
Patent number
US07709505B2

Reaction notes

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