Sodium Hydroxide → 7-(3-(2-Chloro-4-(2,2,2-trifluoroethoxy)phenoxy)propoxy)-chromane-2-carboxylic acid

HRID 51081Notes

Reaction equation

[Cl:1][C:2]1[CH:27]=[C:26]([O:28][CH2:29][C:30]([F:33])([F:32])[F:31])[CH:25]=[CH:24][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][CH:15]([C:19]([O:21]CC)=[O:20])[O:16]2)=[CH:11][CH:10]=1.[OH-].[Na+]>C(O)(C)C>[Cl:1][C:2]1[CH:27]=[C:26]([O:28][CH2:29][C:30]([F:31])([F:33])[F:32])[CH:25]=[CH:24][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][CH:15]([C:19]([OH:21])=[O:20])[O:16]2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a 2 ml isopropanol solution of ethyl 7-(3-(2-chloro-4-(2,2,2-trifluoroethoxy)phenoxy)propoxy)-chromane-2-carboxylate (17 mg, 0.035 mmol) was added 2N aq. sodium hydroxide. This mixture was heated to 70° C. overnight. The solvent was removed under reduced pressure. The residue was diluted with AcOEt and 2N hydrochloric acid. The organic layer was separated, and the aqueous layer was extracted twice with AcOEt. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated to give the title compound 16 mg.

Workup

customThe solvent was removed under reduced pressure
additionThe residue was diluted with AcOEt and 2N hydrochloric acid
customThe organic layer was separated
extractionthe aqueous layer was extracted twice with AcOEt
dry with materialThe combined organic layers were dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-06205d1375d84ab0b016b6ea343d4176
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713508B2

Reaction notes

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