Methyl iodide → HCID 58780214, compound

HRID 1432155Notes

Reaction equation

HRID 1432155 reaction equation
[I:1][C:2]1[C:3]([O:25][CH3:26])=[C:4]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[C:14](I)[C:13]=2[O:23][CH3:24])[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH2:27]([Li])CCC.CI>C1COCC1.[Cl-].[NH4+]>[CH3:26][O:25][C:3]1[C:2]([I:1])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]=1[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[C:14]([CH3:27])[C:13]=1[O:23][CH3:24]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 50459431,1'-Binaphthalene, 3,3'-diiodo-2,2'-dimethoxy-HCID 178418339Butyllithium

Product 1

HCID 58780214HCID 58780214, compound

Reagents, catalysts & solvents 2

HCID 25517Ammonium ChlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a −80° C. solution of (+/−)-3,3′-diiodo-2,2′-dimethoxy-1,1′-binaphthyl (2.016 g, 3.6 mmol) in THF (dry, distilled, 80 mL, 0.044 M) was added n-butyl lithium (2.8 mL, 3.9 mmol) dropwise. The reaction mixture turned yellow and was stirred for 1 h before the addition of methyl iodide (dry, distilled, 0.35 mL, 5.6 mmol). The reaction mixture was allowed to gradually warm to room temperature. After stirring for a further 3 h saturated aqueous ammonium chloride solution (4 drops) was added. The reaction mixture was evaporated to dryness, the residue taken up in diethyl ether and washed with water. The organic layer was dried (MgSO4), filtered and the filtrate evaporated to dryness to give a pale yellow solid. Purification of the crude material by flash column chromatography (4% ethyl acetate/hexane) yielded (+/−)-2,2′-dimethoxy-3-iodo-3′-methyl-1,1′-binaphthyl.

Workup

  1. additionwas added
  2. customThe reaction mixture was evaporated to dryness
  3. washwashed with water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customthe filtrate evaporated to dryness
  7. customto give a pale yellow solid
  8. customPurification of the crude material by flash column chromatography (4% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c72bf09075454cefb658bed1fa4c5860
Source dataset
uspto-grants-2009_11
Patent number
US07612036B2

Reaction notes

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