Tetrabutylammonium Fluoride → HCID 86659569, compound

HRID 1431032Notes

Reaction equation

HRID 1431032 reaction equation
C[Si](C)(C)CC[O:5][C:6](=[O:48])[C:7]1[CH:12]=[C:11]([O:13][CH:14]([CH3:16])[CH3:15])[CH:10]=[C:9]([O:17][C:18]2[CH:23]=[CH:22][C:21]([P:24]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[C:41]([F:47])[CH:40]=3)([O:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([F:36])[CH:29]=3)=[O:25])=[CH:20][CH:19]=2)[CH:8]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CN(C=O)C.CCOC(C)=O>[F:36][C:30]1[CH:29]=[C:28]([CH:33]=[CH:32][C:31]=1[O:34][CH3:35])[CH2:27][O:26][P:24]([C:21]1[CH:22]=[CH:23][C:18]([O:17][C:9]2[CH:8]=[C:7]([CH:12]=[C:11]([O:13][CH:14]([CH3:16])[CH3:15])[CH:10]=2)[C:6]([OH:48])=[O:5])=[CH:19][CH:20]=1)([O:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[C:41]([F:47])[CH:40]=1)=[O:25]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86659570HCID 86659570, compound

Product 1

HCID 86659569HCID 86659569, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-{-4-[bis-(3-fluoro-4-methoxy-benzyloxy)-phosphoryl]-phenoxy}-5-isopropoxy-benzoic acid 2-trimethylsilanyl-ethyl ester (536 mg, 0.735 mmol) in DMF (10 mL) was added tetrabutylammonium fluoride (1.0 M solution in THF) (1.84 mL, 1.84 mmol). Stirred at rt for 16 h. The reaction mixture was diluted with EtOAc and washed with H2O (2×) and brine (2×). Dried with MgSO4 and evaporated solvent to provide 462 mg (100%) of 3-{4-[bis-(3-fluoro-4-methoxy-benzyloxy)-phosphoryl]-phenoxy}-5-isopropoxy-benzoic acid. 1H NMR (300 MHz, DMSO-d6): δ 13.20 (bs, 1H), 7.74 (dd, J=13, 9 Hz, 2H), 7.27 (dd, J=2, 1 Hz, 1H), 7.13 (m, 9H), 6.94 (t, J=2 Hz, 1H), 4.97 (dd, J=9, 2 Hz, 4H), 4.67 (m, 1H), 3.82 (s, 6H), 1.27 (s, J=6 Hz, 6H).

Workup

  1. washwashed with H2O (2×) and brine (2×)
  2. dry with materialDried with MgSO4
  3. customevaporated solvent

Sources & evidence

ORD record
ord-3754eb1e0202409dad4df50bc9f789b9
Source dataset
uspto-grants-2015_01
Patent number
US08940927B2

Reaction notes

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