Methyl iodide → HCID 11557990, compound

HRID 2103013Notes

Reaction equation

HRID 2103013 reaction equation
[CH3:1][C:2]1[C:14]([OH:15])=[C:13]([CH3:16])[C:12]([CH3:17])=[C:11]2[C:3]=1[CH2:4][CH:5]([OH:18])[C:6]1([O:10]2)[CH2:9][CH2:8][CH2:7]1.[H-].[Na+].[CH3:21]I>C1COCC1>[CH3:21][O:18][CH:5]1[C:6]2([CH2:7][CH2:8][CH2:9]2)[O:10][C:11]2[C:3](=[C:2]([CH3:1])[C:14]([OH:15])=[C:13]([CH3:16])[C:12]=2[CH3:17])[CH2:4]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57803526HCID 57803526, compound

Product 1

HCID 11557990HCID 11557990, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tert-butyldimethylsilyl derivative of 5,7,8-trimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutane]-3,6-diol (30 mg), prepared as described in Example 22, in 1 mL of THF was added to NaH (8 mg) suspended in THF (1.5 mL). The resulting mixture was stirred at room temperature for 10 min and methyl iodide (34 mg) was added. The reaction was stirred at room temperature for 10 h and quenched onto 30 g of ice. It was extracted with hexane/EtOAc (2:1, 3×30 mL) and the combined organic layers were washed with brine, dried over Na2SO4 and concentrated to afford the 6-tert-butyldimethylsilyl derivative of 3-methoxy-5,7,8-trimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-ol which was used directly for the next reaction.

Workup

  1. stirringThe reaction was stirred at room temperature for 10 h
  2. customquenched onto 30 g of ice
  3. extractionIt was extracted with hexane/EtOAc (2:1, 3×30 mL)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-292eec152a234bd698c1fb2bed1e42d3
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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