Tetrahydrofuran → HCID 53709988, compound

HRID 266585Notes

Reaction equation

HRID 266585 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([F:13])[C:3]=1[CH:14]([C:21](C)(C)C)CO[Si](C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1C[O:46]CC1>CCOCC>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([F:13])[C:3]=1[CH:14]([OH:46])[CH3:21]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 67717651HCID 67717651, compound

Product 1

HCID 53709988HCID 53709988, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl 4-chloro-2-fluoro-3-(1-t-butyltrimethylsilyloxyethyl)benzoate (25 g) and tetrabutylammonium fluoride (210 ml of 1.0M solution in THF) were dissolved in THF and stirred for 4 hours at room temperature. The mixture was diluted with ether and washed with water. The organic extract was dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness yielding ethyl 4-chloro-2-fluoro-3-(1-hydroxyethyl)benzoate (16.8 g) as a clear oil, NMR (CDCl3) 1.3(t,3H), 1.5(d,3H), 2.5(bs, 1H), 4.3(q,2H), 5.3(q, 1H), 7.1(d, 1H), 7.7(t, 1H).

Workup

  1. washwashed with water
  2. extractionThe organic extract
  3. dry with materialwas dried (anhydrous magnesium sulphate)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-ea6ece056eb74900927ecc6a7e66dc35
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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