Dichloromethane → HCID 22467324, compound

HRID 1934556Notes

Reaction equation

HRID 1934556 reaction equation
N[CH2:2][C:3]1([OH:31])[C:12]2[C:7](=[C:8]([O:13][Si:14]([C:27]([CH3:30])([CH3:29])[CH3:28])([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][CH2:4]1.N([O-])=O.[Na+].C(Cl)Cl>CC(O)=O.O>[Si:14]([O:13][C:8]1[C:7]2[CH2:6][CH2:5][CH2:4][C:3](=[O:31])[CH2:2][C:12]=2[CH:11]=[CH:10][CH:9]=1)([C:27]([CH3:30])([CH3:28])[CH3:29])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 22467287HCID 22467287, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 22467324HCID 22467324, compoundYield 37.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 1-aminomethyl-5-(tert-butyldiphenyl-silyloxy)-1,2,3,4-tetrahydronaphthalen-1-ol (34.5 g) in 20% AcOH (700 ml) was added NaNO2 (7.18 g) in water (60 ml) at 5° C. The mixture was stirred at the same temperature for 2.5 hours. After addition of CH2Cl2 (70 ml), the mixture was stirred for 30 minutes. The reaction mixture was extracted with EtOAc. The organic layer was washed with water and then brine. It was dried over magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (hexane-EtOAc 10:1) to give 1-(tert-butyldiphenylsilyloxy)-6,7,8, 9-tetrahydro-5H-benzocyclohepten-6-one (12.52 g).

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. extractionThe reaction mixture was extracted with EtOAc
  3. washThe organic layer was washed with water
  4. dry with materialIt was dried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (hexane-EtOAc 10:1)

Sources & evidence

ORD record
ord-eca6eb8b50944d65a58197ecbc35b028
Source dataset
uspto-grants-2002_05
Patent number
US06384072B1

Reaction notes

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