Tetrabutylammonium Fluoride → Methyl 2-((S)-6-((R)-7-fluoro-4-(4-hydroxy-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

HRID 237447Notes

Reaction equation

HRID 237447 reaction equation
[Si]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:24]=[CH:23][C:22]([F:25])=[C:21]3[C:17]=2[CH2:18][CH2:19][C@H:20]3[O:26][C:27]2[CH:40]=[CH:39][C:30]3[C@H:31]([CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH2:32][O:33][C:29]=3[CH:28]=2)=[C:11]([CH3:41])[CH:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)C>[F:25][C:22]1[CH:23]=[CH:24][C:16]([C:12]2[C:13]([CH3:15])=[CH:14][C:9]([OH:8])=[CH:10][C:11]=2[CH3:41])=[C:17]2[C:21]=1[C@H:20]([O:26][C:27]1[CH:40]=[CH:39][C:30]3[C@H:31]([CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH2:32][O:33][C:29]=3[CH:28]=1)[CH2:19][CH2:18]2

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86697112Methyl 2-((S)-6-((R)-4-(4-(tert-butyldimethylsilyloxy)-2,6-dimethylphenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

Product 1

HCID 86697113Methyl 2-((S)-6-((R)-7-fluoro-4-(4-hydroxy-2,6-dimethylphenyl)-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 2-((S)-6-((R)-4-(4-(tert-butyldimethylsilyloxy)-2,6-dimethylphenyl)-7-fluoro-2,3-dihydro-1H-inden-1-yloxy)-2,3-dihydrobenzofuran-3-yl)acetate (440 mg) in tetrahydrofuran (5 mL) is added at 0° C. tetrabutylammonium fluoride (3.1 mL of a 1 M solution in tetrahydrofuran). The mixture is stirred for 2 hours at room temperature, diluted with diethylether and washed with water and brine. After drying (MgSO4) the solvents are evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→60:40) to give the title compound. Yield: 280 mg; LC (method 4): tR=1.79 min; Mass spectrum (ESI+): m/z=485 [M+Na].

Workup

  1. washwashed with water and brine
  2. dry with materialAfter drying (MgSO4) the solvents
  3. customare evaporated
  4. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 90:10→60:40)

Sources & evidence

ORD record
ord-70d4974d8a8e45338ec0d2da565041b5
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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