Isopropanol → 3-(2-Carboxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indan-2-ylacetic acid

HRID 862364Notes

Reaction equation

HRID 862364 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH2:19][CH2:20][CH3:21])[CH:16]=3)[CH:11]([C:22]3[CH:27]=[CH:26][C:25]4[O:28][CH2:29][O:30][C:24]=4[CH:23]=3)[CH:10]2C(O)=O)=[C:5]([O:34][CH2:35]OC)[CH:4]=1.COC1C=CC(C2C3C(=CC=C(OCCC)C=3)C(C3C=CC4OCOC=4C=3)[CH:47]2[C:68]([O-:70])=[O:69])=C(OCOC)C=1.[OH-:75].[Na+].[CH:77]([OH:80])(C)C>>[C:77]([CH2:35][O:34][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[CH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH2:19][CH2:20][CH3:21])[CH:16]=2)[CH:11]([C:22]2[CH:27]=[CH:26][C:25]3[O:28][CH2:29][O:30][C:24]=3[CH:23]=2)[CH:10]1[CH2:47][C:68]([OH:70])=[O:69])([OH:80])=[O:75]

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 14798Sodium HydroxideHCID 187038763-(4Methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylateHCID 187038773-(4-Methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid

Product 1

HCID 101663713-(2-Carboxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indan-2-ylacetic acidYield 84%

Procedure

(1RS, 2SR, 3RS)-3-(4-Methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid. A solution of methyl (1RS, 2RS, 3RS)-3-(4-methoxy-2-methoxymethoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylate (2.42 g, 4.6 mmol) in isopropyl alcohol (30 ml) with aqueous NaOH (8 ml of 5N solution) was refluxed for 4 h. The resultant mixture was partitioned between EtOAc and 3N HCl. The organic extract was washed with H2O then brine, dried (Na2SO4) and solvent removed in vacuo to afford the title compound as a colorless oil (1.98 g, 84%).

Workup

  1. customThe resultant mixture was partitioned between EtOAc and 3N HCl
  2. extractionThe organic extract
  3. washwas washed with H2O
  4. dry with materialbrine, dried (Na2SO4) and solvent
  5. customremoved in vacuo

Sources & evidence

ORD record
ord-53ad9e5afbe54c55abd2e7dfda602e29
Source dataset
uspto-grants-1998_02
Patent number
US05716984

Reaction notes

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