Diiodomethane → HCID 54414098, compound

HRID 344052Notes

Reaction equation

HRID 344052 reaction equation
[Si:1]([O:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH2:21][CH2:22][C:23]([CH2:29][OH:30])=[CH:24]2)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:31]([Zn]CC)C.ICI.C(OCC)(=O)C>C1C=CC=CC=1.O>[Si:1]([O:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:25]2[C:20]=1[CH2:21][CH2:22][C:23]1([CH2:29][OH:30])[CH2:31][CH:24]12)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6346DiiodomethaneHCID 8857Ethyl AcetateHCID 53727654HCID 53727654, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 54414098HCID 54414098, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a solution of 5-t-butyldiphenylsilyloxy-2-hydroxymethyl-3,4-dihydronaphthalene (1.0 g) in benzene (10 ml) were added diethylzinc (7.2 ml, 1M solution in hexane) and diiodomethane (1.2 ml) at 0° C. under N2. After being stirred for 4 hours at room temperature, the solution was poured into a mixture of ethyl acetate and water. The organic layer was washed with 1N-HCl solution, sat. NaHCO3, and brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford 5-t-butyldiphenylsilyloxy-1,2-methylene-2-hydroxymethyl-1,2,3,4-tetrahydronaphthalene.

Workup

  1. washThe organic layer was washed with 1N-HCl solution, sat. NaHCO3, and brine
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-9a8102a7f0854c35b2ba4f2e678b984a
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Reaction notes

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