Lithium hydroxide, monohydrate → HCID 71711265, compound

HRID 1468401Notes

Reaction equation

HRID 1468401 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:43])[CH2:7][C:8]1[C:17]([CH3:18])=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([C:28]3[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[C:30]([C:38]([F:41])([F:40])[F:39])[CH:29]=3)(=[O:27])=[O:26])=[CH:21][CH:20]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:42])[CH:14]=2)[CH:9]=1>C1COCC1.O>[F:37][C:34]([F:35])([F:36])[C:32]1[CH:33]=[C:28]([S:25]([C:22]2[CH:21]=[CH:20][C:19]([C:16]3[C:15]4[C:10](=[CH:11][CH:12]=[C:13]([Cl:42])[CH:14]=4)[CH:9]=[C:8]([CH2:7][C:6]([OH:43])=[O:5])[C:17]=3[CH3:18])=[CH:24][CH:23]=2)(=[O:26])=[O:27])[CH:29]=[C:30]([C:38]([F:39])([F:40])[F:41])[CH:31]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86694996HCID 86694996, compound

Product 1

HCID 71711265HCID 71711265, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide monohydrate (0.011 g, 0.26 mmol) was added to a stirred solution of {4-[4-(3,5-bis-trifluoromethyl-benzenesulfonyl)-phenyl]-6-chloro-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (0.038 g, 0.063 mmol) in a 3:1 THF—H2O mixture (4 mL). The reaction mixture was stirred for 16 hours at room temperature. The THF was distilled off under reduced pressure, and the crude residue was diluted with water, acidified [pH˜2] via the drop-wise addition of an aqueous solution of hydrochloric acid (6.0 N). The mixture was extracted twice with ethyl acetate. The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. Trituration with hexanes afforded {4-[4-(3,5-bis-trifluoromethyl-benzenesulfonyl)-phenyl]-6-chloro-3-methyl-naphthalen-2-yl}-acetic acid (0.031 g, 84%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.49 (br. s, 1 H) 8.71 (s, 2 H) 8.59 (s, 1 H) 8.35 (d, J=7.82 Hz, 2 H) 7.97 (d, J=8.40 Hz, 1 H) 7.91 (s, 1 H) 7.58 (d, J=7.82 Hz, 2 H) 7.48 (d, J=8.60 Hz, 1 H) 6.95 (s, 1 H) 3.84 (s, 2 H) 2.03 (s, 3 H). MS calcd. for C27H16ClF6O4S [(M−H)−] 585, obsd. 585.3.

Workup

  1. distillationThe THF was distilled off under reduced pressure
  2. additionthe crude residue was diluted with water
  3. additionvia the drop-wise addition of an aqueous solution of hydrochloric acid (6.0 N)
  4. extractionThe mixture was extracted twice with ethyl acetate
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude product

Sources & evidence

ORD record
ord-1a91f33810104cb8a195fc088e9e1c8d
Source dataset
uspto-grants-2015_04
Patent number
US09000044B2

Reaction notes

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