Diiodomethane → Methyl 1-(iodomethyl)cyclohexanecarboxylate

HRID 1160145Notes

Reaction equation

HRID 1160145 reaction equation
[Li]CCCC.[CH3:6][O:7][C:8]([CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:9].[I:16][CH2:17]I>C1COCC1>[CH3:6][O:7][C:8]([C:10]1([CH2:17][I:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:9]

Participants

5

Reactant 3

HCID 6346DiiodomethaneHCID 20748Methyl cyclohexanecarboxylateHCID 178418339Butyllithium

Product 1

HCID 58947958Methyl 1-(iodomethyl)cyclohexanecarboxylateYield 113.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a −78° C. of Diisoprpyl amine (132 mmol, 18.65 mL) in THF (100 mL) was added n-BuLi (120 mmol, 75 mL). Cold bath was removed and put back after 30 minutes. Cyclohexane carboxylic acid methyl ester 1261-A (15.57 g, 109 mmol) was added dropwise in THF (50 mL). After 1 h, Diiodomethane (109 mmol, 8.78 mL) was added while keeping temperature below 10° C. After addition, reaction was warmed to RT and stirred overnight. After 18 h, reaction was quenched with NH4Cl and extracted with EtOAc. Washed with brine, dried over MgSO4, filtered and concentrated down to provide 35 g of product 1261-B.

Workup

  1. customCold bath was removed
  2. waitAfter 1 h
  3. customtemperature below 10° C
  4. additionAfter addition, reaction
  5. waitAfter 18 h
  6. customreaction
  7. customwas quenched with NH4Cl
  8. extractionextracted with EtOAc
  9. washWashed with brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated down

Sources & evidence

ORD record
ord-4f7e41d935dc44c0a81f56c0d1c9a1b8
Source dataset
uspto-grants-2010_10
Patent number
US07816326B2

Reaction notes

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