Hydrochloric Acid → HCID 57557635, compound

HRID 2237767Notes

Reaction equation

HRID 2237767 reaction equation
[C:1]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[F:13][C:14]1[CH:15]=[C:16]([C:24](OC)=[O:25])[C:17]([C:20](OC)=[O:21])=[CH:18][CH:19]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl>C1COCC1>[F:13][C:14]1[CH:15]=[C:16]2[C:17](=[CH:18][CH:19]=1)[C:20]([OH:21])=[C:2]([C:1]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:24]2[OH:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 31249Diethyl SuccinateHCID 2733832Lithium HexamethyldisilazideHCID 22744505Dimethyl 4-fluorobenzene-1,2-dicarboxylate

Product 1

HCID 57557635HCID 57557635, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl succinate (16.26 ml, 98.1 mmol) was added to dimethyl 4-fluoro-1,2-benzenedicarboxylate (10.4 g, 49.1 mmol) and LHMDS (1M in THF, 196 ml, 196 mmol) in THF (150 ml) at 10° C. (internal) over 30 minutes. Allowed to warm to room temperature slowly. After 20 hours, 2M HCl (˜500 ml) was added to acidify to pH 5. The mixture was extracted with EtOAc, then the organics washed with water, brine, dried over magnesium sulphate and concentrated in vacuo to give a brown oil. This was purified by chromatography on silica gel eluting with EtOAc/hexane (2:98) to yield the title compound as a yellow solid (4.58 g, 14.2 mmol).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. washthe organics washed with water, brine
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customto give a brown oil
  6. customThis was purified by chromatography on silica gel eluting with EtOAc/hexane (2:98)

Sources & evidence

ORD record
ord-4e841ba7bd894b97acd86997aa3790ff
Source dataset
uspto-grants-2010_05
Patent number
US07718689B2

Reaction notes

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