Ammonium Chloride → HCID 66936618, compound

HRID 1364000Notes

Reaction equation

HRID 1364000 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH2:5][CH2:6][C:7]1([CH2:13][C:14]([O:16]C)=O)[CH2:12][CH2:11][CH2:10][CH:9]=[CH:8]1.N([Li])(C(C)C)C(C)C.[NH4+].[Cl-]>C1COCC1>[CH3:1][O:2][C:3]([C:4]1[CH2:5][CH2:6][C:7]2([CH2:12][CH2:11][CH2:10][CH:9]=[CH:8]2)[CH2:13][C:14]=1[OH:16])=[O:18]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 66936810HCID 66936810, compoundHCID 178506924HCID 178506924, compound

Product 1

HCID 66936618HCID 66936618, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the relevant 4-(1-methoxycarbonylmethyl-cyclohex-2-enyl)-butyric acid methyl ester isomer (8) or (8′) (31.0 g, 122 mmol) in dry THF (580 mL) at −78° C. was added dropwise i-Pr2NLi (2 M solution in n-heptane; 122 mL, 244 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 2 hours. A saturated NH4Cl solution (700 mL) was added and the aqueous layer repeatedly extracted with Et2O. The combined organic layers were dried over anhydrous MgSO4 and the solvents removed in vacuo. The resulting residue was purified over silica (n-pentane/Et2O, 95:5) to afford 24.7 g (91% yield) of the desired product as white crystals which were characterized as follows:

Workup

  1. extractionthe aqueous layer repeatedly extracted with Et2O
  2. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  3. customthe solvents removed in vacuo
  4. customThe resulting residue was purified over silica (n-pentane/Et2O, 95:5)

Sources & evidence

ORD record
ord-799e26e1062a42fb850faf8af422e684
Source dataset
uspto-grants-2011_02
Patent number
US07888338B2

Reaction notes

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