Methyl iodide → HCID 68854301, compound

HRID 1986512Notes

Reaction equation

HRID 1986512 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:7][CH2:6][C:5]([CH:8]([CH3:11])[CH2:9][OH:10])=[C:4]2[C:12]([CH3:18])([CH3:17])[CH:13]3[CH2:16][C:3]12[CH2:15][CH2:14]3.[CH2:20]1COCC1.[H-].[Na+].CI>CN(C=O)C>[CH3:20][O:10][CH2:9][CH:8]([C:5]1[CH2:6][CH2:7][C:2]([CH3:1])([CH3:19])[C:3]23[CH2:16][CH:13]([CH2:14][CH2:15]2)[C:12]([CH3:18])([CH3:17])[C:4]=13)[CH3:11]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 688525241,3,4,5,6,7-Hexahydro-β,1,1,5,5-pentamethyl-2H-2,4a-methanonaphthalene-8-ethanol

Product 1

HCID 68854301HCID 68854301, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3b (1.0 g, 3.8×10−3 mol) in DMF (5 ml) was added to a THF (8 ml) suspension of sodium hydride (0.27 g of 50% dispersion in mineral oil, washed twice with hexane, 5.6×10−3 mol). After 3 h stirring at r. t., methyl iodide (1.6 g, 0.011 mol) was added under cooling and the reaction mixture was stirred at r. t. for additional 4 h, poured into ice-cold 2M HCl (100 ml) and extracted with MTBE (2×100 ml). The organic phase was washed with brine (2×50 ml), dried (MgSO4), concentrated in vacuo and purified by flash chromatography (MTBE/hexane 1:20) to give 5-(1-methoxyprop-2-yl)-2,2,7,7-tetramethyltricyclo[6.2.1.01,6]undec-5-ene (8b, 0.73 g, 69% yield, colourless oil).

Workup

  1. washwashed twice with hexane, 5.6×10−3 mol)
  2. temperatureunder cooling
  3. stirringthe reaction mixture was stirred at r
  4. waitfor additional 4 h
  5. extractionextracted with MTBE (2×100 ml)
  6. washThe organic phase was washed with brine (2×50 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. custompurified by flash chromatography (MTBE/hexane 1:20)

Sources & evidence

ORD record
ord-be36bfa5d7be4cb490f7152e429f94ef
Source dataset
uspto-grants-2009_06
Patent number
US07550417B2

Reaction notes

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