Methyl iodide → HCID 22026353, compound

HRID 1793231Notes

Reaction equation

HRID 1793231 reaction equation
[CH3:1][C:2]1([OH:15])[C:7]([CH3:13])([CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11])[CH2:6][CH2:5][CH:4]=[C:3]1[CH3:14].[Li][CH2:17]CCC.CI>C1COCC1>[CH3:17][O:15][C:2]1([CH3:1])[C:3]([CH3:14])=[CH:4][CH2:5][CH2:6][C:7]1([CH3:13])[CH2:8][CH:9]=[C:10]([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 22026342HCID 22026342, compoundHCID 178418339Butyllithium

Product 1

HCID 22026353HCID 22026353, compoundYield 93.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,2,6-trimethyl-6-(3-methyl-but-2-enyl)-cyclohex-2-enol (5.00 g, 24.0 mmol) in THF (80 ml) was added n-BuLi (1.6M in hexane, 16.5 ml, 26.4 mmol) at 0° C. After the mixture was stirred for 30 min, methyl iodide (5.18 g, 36.5 mmol) was added. The mixture was stirred at room temperature over night and then poured on ice and extracted with MTBE. The organic phase was washed with H2O and brine, dried (MgSO4) and concentrated in vacuo. The residue was distilled (bp. 75° C./0.2 Torr) to yield 5.0 g (93%) of an colorless oil containing 2 isomers: 1H-NMR (400 MHz, CDCl3): 5.64 (bs, 1H, 2-H), 5.23-5.15 (m, 1H, CH2CH═C(CH3)2), 3.30, 3.28 (2s, 3H, O—CH3), 2.22-2.12 (m, 1H), 1.99-1.88 (m, 3H), 1.75-1.58 (m, 10H), 1.20,1.18 (2s, 3H), 0.93, 0.79 (2s, 3H) ppm. MS (EI): 222 (M+, 1), 190 (11), 175 (10), 147 (60), 121 (100), 112 (30), 105 (57), 91 (40), 79 (25), 69 (14), 41 (45). IR (ATR): 2966s, 2926s, 1449s, 1377s, 1083vs, 858m cm−1.

Workup

  1. stirringThe mixture was stirred at room temperature over night
  2. additionpoured on ice
  3. extractionextracted with MTBE
  4. washThe organic phase was washed with H2O and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. distillationThe residue was distilled (bp. 75° C./0.2 Torr)

Sources & evidence

ORD record
ord-dd44bcdd9c8945a98b0da8058f632e23
Source dataset
uspto-grants-2006_07
Patent number
US07078570B2

Reaction notes

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