Citric Acid → HCID 58687939, compound

HRID 132850Notes

Reaction equation

HRID 132850 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[C:15](Br)=[C:14]([C:17]([F:20])([F:19])[F:18])[N:13]=[C:12]([O:21][CH3:22])[C:11]=1[Br:23])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1([Li])C=CC=CC=1.C1CCCCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1.C(OCC)C>[Br:23][C:11]1[C:12]([O:21][CH3:22])=[N:13][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:15][C:10]=1[CH2:9][O:8][Si:1]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 8078CyclohexaneHCID 58687972HCID 58687972, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 58687939HCID 58687939, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the compound from Step E above (2.68 g, 3.41 mmol) in tetrahydrofuran (50 mL) at −78° C. was added 2.0M phenyllithium in cyclohexane (1.70 mL, 3.41 mmol). After the reaction was stirred for 5 min, 10% citric acid in THF was added. The mixture was diluted with ethyl ether, washed sequentially with water and saturated brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography (silica gel; 10 to 15% ethyl acetate/hexanes gradient elution) to yield the title compound. 1H NMR (400 MHz, CDCl3) δ 7.52 (s, 1H), 4.74 (s, 2H), 4.08 (s, 3H), 0.99 (s, 9H), 0.17 (s, 6H). LC/MS: 400/402 (M+H and M+H+2).

Workup

  1. washwashed sequentially with water and saturated brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography (silica gel; 10 to 15% ethyl acetate/hexanes gradient elution)

Sources & evidence

ORD record
ord-8e1ba72b74644726915d8611c08062d7
Source dataset
uspto-grants-2008_06
Patent number
US07388019B2

Reaction notes

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