Trifluoroacetic acid → 4-(6-Cyano-4-(methoxycarbonyl)chroman-7-yloxy)-3-methylbenzoic acid

HRID 1626401Notes

Reaction equation

HRID 1626401 reaction equation
C([O:5][C:6]([C:8]1[CH:30]=[CH:29][C:11]([O:12][C:13]2[CH:22]=[C:21]3[C:16]([CH:17]([C:23]([O:25][CH3:26])=[O:24])[CH2:18][CH2:19][O:20]3)=[CH:15][C:14]=2[C:27]#[N:28])=[C:10]([CH3:31])[CH:9]=1)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[C:27]([C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:13]=1[O:12][C:11]1[CH:29]=[CH:30][C:8]([C:6]([OH:7])=[O:5])=[CH:9][C:10]=1[CH3:31])[O:20][CH2:19][CH2:18][CH:17]2[C:23]([O:25][CH3:26])=[O:24])#[N:28]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67288331Methyl 7-(4-(tert-butoxycarbonyl)-2-methylphenoxy)-6-cyanochroman-4-carboxylate

Product 1

HCID 670807034-(6-Cyano-4-(methoxycarbonyl)chroman-7-yloxy)-3-methylbenzoic acidYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 7-(4-(tert-butoxycarbonyl)-2-methylphenoxy)-6-cyanochroman-4-carboxylate was taken up in dichloromethane (10 mL). To the solution was added 2 ml TFA and the solution was stirred at ambient temperature for 2 hours. The reaction was concentrated and the crude material was purified over silica gel, eluting with 2-3% methanol/dichloromethane, to provide the desired product (0.103 g, 89%).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe crude material was purified over silica gel
  3. washeluting with 2-3% methanol/dichloromethane

Sources & evidence

ORD record
ord-66a8027330974f289c3155025287ee44
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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