HCID 11688361, compound → HCID 18475007, compound

HRID 2227890Notes

Reaction equation

HRID 2227890 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:25][CH:24]=2)[C:17]([O:19][CH3:20])=[O:18])=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C>C1COCC1>[C:32]([O:31][C:29]([C:26]1[CH:25]=[CH:24][C:23]([CH2:22][O:21][CH:16]([CH2:15][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)[C:17]([O:19][CH3:20])=[O:18])=[CH:28][CH:27]=1)=[O:30])([CH3:35])([CH3:33])[CH3:34]

Participants

4

Reactant 2

HCID 11688361HCID 11688361, compoundHCID 18474995HCID 18474995, compound

Product 1

HCID 18475007HCID 18475007, compoundYield 108.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 3-(4-tert-butyldimethylsilyloxyphenyl)-2-[(4-tert-butoxycarbonylphenyl)methoxy]propionate (310 mg, 0.61 mmol) in THF (5 ml) at −20° C. was treated with tetrabutylammonium fluoride-acetic acid (1.0M in THF, 0.76 ml, 0.76 mmol). The mixture was stirred at this temperature for 15 minutes, quenched with saturated aqueous sodium bicarbonate and extracted with diethyl ether. The organic phase was washed with brine, dried over sodium sulfate and concentrated in vacuo to give the title material (256 mg, 100%) as a pale yellow oil.

Workup

  1. customquenched with saturated aqueous sodium bicarbonate
  2. extractionextracted with diethyl ether
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aeb562316b4f44539f7aceccf2c775b8
Source dataset
uspto-grants-2002_07
Patent number
US06414179B1

Reaction notes

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