Hydrochloric Acid → HCID 22467317, compound

HRID 1934559Notes

Reaction equation

HRID 1934559 reaction equation
[Si:1]([O:18][C:19]1[C:24]2[CH2:25][CH2:26][CH2:27][CH:28]([CH2:30][OH:31])[CH2:29][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.[C:32]1([N:38]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:39](Cl)=[O:40])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.Cl>N1C=CC=CC=1>[C:32]1([N:38]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:39](=[O:40])[O:31][CH2:30][CH:28]2[CH2:27][CH2:26][CH2:25][C:24]3[C:19]([O:18][Si:1]([C:14]([CH3:15])([CH3:16])[CH3:17])([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:20][CH:21]=[CH:22][C:23]=3[CH2:29]2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 65741N,N-Diphenylcarbamic chlorideHCID 22467310HCID 22467310, compound

Product 1

HCID 22467317HCID 22467317, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of [1-(tert-butyldiphenylsilyloxy)-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl]methanol (200 mg) and diphenylcarbamoyl chloride (324 mg) in pyridine (5 ml) was stirred at 100° C. for 48 hours. After cooling, the reaction mixture was poured into 6N-hydrochloric acid (13 ml) under ice-cooling and 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 15:1 to 10:1) to give [1-(tert-butyldiphenylsilyloxy)-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl]methyl N,N-diphenylcarbamate (262.7 mg) as an amorphous solid.

Workup

  1. temperatureAfter cooling
  2. temperaturecooling
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water, saturated sodium hydrogencarbonate solution, water
  5. dry with materialIt was dried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane-EtOAc 15:1 to 10:1)

Sources & evidence

ORD record
ord-2bcf82a302444a34ae882d3bd93e576e
Source dataset
uspto-grants-2002_05
Patent number
US06384072B1

Reaction notes

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