Hydrochloric Acid → HCID 22467306, compound

HRID 1934561Notes

Reaction equation

HRID 1934561 reaction equation
[Si:1]([O:18][C:19]1[C:24]2[CH2:25][CH2:26][CH2:27][C:28]([CH2:30][OH:31])=[CH:29][C:23]=2[CH:22]=[CH:21][CH:20]=1)([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.[Si](OC1C2CCC=C(CO)CC=2C=CC=1)(C(C)(C)C)(C1C=CC=CC=1)[C:33]1C=CC=CC=1.[Zn](CC)CC.ICI.Cl>C(Cl)Cl>[Si:1]([O:18][C:19]1[C:24]2[CH2:25][CH2:26][CH2:27][C:28]3([CH2:30][OH:31])[CH2:33][CH:29]3[C:23]=2[CH:22]=[CH:21][CH:20]=1)([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 5

HCID 313Hydrochloric AcidHCID 6346DiiodomethaneHCID 22467281HCID 22467281, compoundHCID 22467284HCID 22467284, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 22467306HCID 22467306, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of a mixture of [1-(tert-butyldiphenylsilyloxy)-8,9-dihydro-7H -benzocyclohepten-6-yl]methanol and [1-(tert-butyldiphenylsilyloxy)-8,9-dihydro-5H-benzocyclohepten-6-yl]methanol (891 mg) in CH2Cl2 (10 ml) were added Et2Zn (1.0M hexane solution, 6.24 ml) and diiodomethane (0.838 ml) at −10 to −30° C. The mixture was stirred at the same temperature for 30 minutes. Then after warming to room temperature, the mixture was stirred for 8 hours. After addition of 1N-hydrochloric acid at 5° C., the resultant was extracted with EtOAc. The organic layer was washed with water, saturated sodium hydrogencarbonate solution, water, and then brine. It was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc 3:1) to give [5-(tert-butyldiphenylsilyloxy)-1,1a,2,3,4,8b-hexahydrobenzo[a]cyclopropa[c]cyclohepten-1a-yl]methanol (646.7 mg) as an amorphous solid.

Workup

  1. stirringthe mixture was stirred for 8 hours
  2. extractionthe resultant was extracted with EtOAc
  3. washThe organic layer was washed with water, saturated sodium hydrogencarbonate solution, water
  4. dry with materialIt was dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (hexane-EtOAc 3:1)

Sources & evidence

ORD record
ord-3d5ad7f9c64d41d983e8d6b0a225b6a5
Source dataset
uspto-grants-2002_05
Patent number
US06384072B1

Reaction notes

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