Triethylsilane → 1-(4-Methoxyphenyl)-3-(3,4-methylenedioxyphenyl)indane-2-carboxylic acid

HRID 650742Notes

Reaction equation

O[C:2]1([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[CH:16]=[CH:15][C:14]3[O:17][CH2:18][O:19][C:13]=3[CH:12]=2)=[C:3]1[C:20]([O-:22])=[O:21].C([SiH](CC)CC)C.[B]>C(Cl)Cl>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([CH:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]([C:11]3[CH:16]=[CH:15][C:14]4[O:17][CH2:18][O:19][C:13]=4[CH:12]=3)[CH:3]2[C:20]([OH:22])=[O:21])=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl (1R)2R)-1-hydroxy-1-(4-methoxyphenyl)-3-(3,4-methylenedioxyphenyl)-indene-2-carboxylate (0.80 g, 1.9 mmol) in CH2Cl2 (10 ml) at 0° C. under an argon atmosphere was added triethylsilane (0.28 a, 2.4 mmol), followed by boron tritluoride etherate (1 ml, 8.1 mmol). The resulting solution was stirred at 0° C. for 10 min, and was then partitioned between EtOAc and 3M HCl. The organic extract was washed with saturated aqueous NaCl and dried (MgSO4). The solvent was removed in vacun, and the residue was filtered through a pad of silica gel, eluting with CH2Cl2. The title compound (mixture of Δ1 and Δ2 double bond isomers) was obtained as a glassy, yellow solid (0.72 g, 94%).

Workup

customwas then partitioned between EtOAc and 3M HCl
extractionThe organic extract
washwas washed with saturated aqueous NaCl
dry with materialdried (MgSO4)
customThe solvent was removed in vacun
filtrationthe residue was filtered through a pad of silica gel
washeluting with CH2Cl2

Sources & evidence

ORD record: ord-8b5eb771d1c74507bb1912415c17a641
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06274737B1

Reaction notes

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