Diiodomethane → HCID 54414098, compound

HRID 963711Notes

Reaction equation

HRID 963711 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
  2. dry with materialHCl solution, sat. NaHCO3, and brine, dried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7c1e5f6b2e0d499babff518e484327a6
Source dataset
uspto-grants-1998_06
Patent number
US05763489

Reaction notes

Loading…