Citric Acid → HCID 18630071, compound

HRID 377980Notes

Reaction equation

HRID 377980 reaction equation
[Li][CH:2]([CH2:4][CH3:5])[CH3:3].C1CCCCC1.CN(CCN(C)C)C.[CH2:20]([N:22]([CH2:32][CH3:33])[C:23](=[O:31])C1C=CC=C(F)C=1)[CH3:21].[F:34][C:35]1C=C(C=C[CH:43]=1)C(O)=O.C(NCC)C.[Si:49](Cl)([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:51])[CH3:50].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[CH3:53][C:52]([Si:49]([CH3:51])([CH3:50])[C:3]1[C:35]([F:34])=[CH:43][CH:5]=[CH:4][C:2]=1[C:23]([N:22]([CH2:20][CH3:21])[CH2:32][CH3:33])=[O:31])([CH3:55])[CH3:54]

Participants

10

Reactant 8

HCID 311Citric AcidHCID 8021DiethylamineHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8078CyclohexaneHCID 99683-Fluorobenzoic AcidHCID 28928tert-Butyldimethylsilyl chlorideHCID 963334N,N-diethyl-3-fluorobenzamideHCID 178418400CID 53628100

Product 1

HCID 18630071HCID 18630071, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

1.3M s-BuLi in cyclohexane (7.7 mL, 0.01 mol) was added dropwise to THF (30 mL) and TMEDA (1.28 g, 0.011 mol) cooled to -78° C. under nitrogen with stirring. To this mixture was added 0.0097 mol of N,N-diethyl-3-fluorobenzamide (prepared from 3-fluorobenzoic acid and diethylamine according to the procedures of the examples of b and f) dissolved in a minimum amount of THF dropwise. The mixture was stirred for 10 min and injected with t-butyldimethylsilylchloride (3.01 g, 0.02 mol). The reaction mixture was stirred and warmed to RT overnight. 25% citric acid (15 mL) was added and the mixture was extracted three times with ether. The ether extracts were combined and washed twice with water, dried (MgSO4), concentrated, and purified by RC eluting with 7:15 ethyl acetate/hexanes. The title compound was recovered as a tan solid in 81% yield. m.p. 50-51° C.

Workup

  1. stirringThe mixture was stirred for 10 min
  2. stirringThe reaction mixture was stirred
  3. temperaturewarmed to RT overnight
  4. extractionthe mixture was extracted three times with ether
  5. washwashed twice with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. custompurified by RC
  9. washeluting with 7:15 ethyl acetate/hexanes
  10. customThe title compound was recovered as a tan solid in 81% yield

Sources & evidence

ORD record
ord-9cc4f4bad3844a6796ac15e5d35db9cc
Source dataset
uspto-grants-2000_02
Patent number
US06028101

Reaction notes

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