Water → HCID 18971692, compound

HRID 2395384Notes

Reaction equation

HRID 2395384 reaction equation
[Si:1]([O:8][C:9]1[C:10]([F:16])=[C:11](O)[CH:12]=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Li])(CC)C.[C:22](=[O:24])=[O:23].C(OCC)C.O>C1COCC1>[Si:1]([O:8][C:9]1[C:10]([F:16])=[C:11]([CH:12]=[CH:13][CH:14]=1)[C:22]([OH:24])=[O:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 18971711HCID 18971711, compoundHCID 86742199Dry ice diethyl etherHCID 178418400CID 53628100

Product 1

HCID 18971692HCID 18971692, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of 3-tert-butyldimethylsilyloxy-2-fluorophenol (10.59 g, 46.8 mmol) in THF (150 ml) cooled to -70° C. was added dropwise over 5 min. sec-butyllithium (42 ml, 1.12M in cyclohexane). The reaction mixture was stirred ad -70° C. for 1 h and then poured into a slurry of dry-ice/diethyl ether. Water (200 ml) was added cautiously and the organic layer separated and discarded. The aqueous layer was acidified to pH 2 with concentrated HCl and extracted with ethyl acetate (3×100 ml). The combined organic extracts were dried (MgSO4) and evaporated to afford title compound (7.90 g, 70%) as a white solid.

Workup

  1. customthe organic layer separated
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-70782938888b47ce8b2f72459843d83f
Source dataset
uspto-grants-1998_09
Patent number
US05814648

Reaction notes

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