Diiodomethane → HCID 18980637, compound

HRID 2392944Notes

Reaction equation

HRID 2392944 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6](/[CH:14]=[CH:15]\[CH2:16][OH:17])[CH:5]=[CH:4][C:3]1=2.[CH2:19](I)I>CCOCC.[Zn].Cl[Cu]>[CH3:1][C:2]1([CH3:18])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([CH:14]3[CH2:19][CH:15]3[CH2:16][OH:17])[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 2

HCID 6346DiiodomethaneHCID 67563960HCID 67563960, compound

Product 1

HCID 18980637HCID 18980637, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 62652Cuprous chlorideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

12.5 g of Zn-dust (activated by washing with HCl, H2O, EtOH, acetone, and EtOEt) and 1.89 g of freshly purified CuCl were refluxed in 120 ml of abs. EtOEt for 20 minutes. After cooling, 18.0 g of (Z)-3-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-prop-2-en-1-ol, dissolved in 40 ml of EtOEt, were added, followed by 15.2 ml of CH2I2. The mixture was kept under reflux for 16 hours. Afterwards, it was poured onto crashed ice, extracted with EtOEt, washed with H2O, and dried over Na2SO4. Evaporation of the solvent and ensuing flash chromatography (silica gel, hexane/AcOEt=90:10) yielded 11.28 g of (1RS,2SR)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-cyclopropylmethanol as yellowish oil (GC-purity: 97.6%).

Workup

  1. temperatureAfter cooling
  2. additionwere added
  3. temperatureunder reflux for 16 hours
  4. additionAfterwards, it was poured
  5. extractionextracted with EtOEt
  6. washwashed with H2O
  7. dry with materialdried over Na2SO4
  8. customEvaporation of the solvent

Sources & evidence

ORD record
ord-b153e9a2adc94e2b9ed94f4689bda122
Source dataset
uspto-grants-1998_09
Patent number
US05801253

Reaction notes

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