Hydrochloric Acid → HCID 57771610, compound

HRID 2070607Notes

Reaction equation

HRID 2070607 reaction equation
[Si:1]([O:8][CH2:9][CH:10]1[CH2:21][CH2:20][C:13]2([CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]2)[CH2:12][CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:25].Cl>CN(C)C=O>[C:4]([Si:1]([O:8][CH2:9][CH:10]1[CH2:21][CH2:20][C:13]2([CH2:14][CH2:15][CH:16]([O:19][CH3:25])[CH2:17][CH2:18]2)[CH2:12][CH2:11]1)([CH3:3])[CH3:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 19390047HCID 19390047, compound

Product 1

HCID 57771610HCID 57771610, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 9-(tert-butyldimethylsilanyloxymethyl)-spiro[5.5]undecan-3-ol (309 mg) obtained in Step 4 in N,N-dimethylformamide (5 mL) was added 60% sodium hydride (60 mg) under ice-cooling, followed by stirring the reaction mixture at room temperature for 5 minutes. To the reaction mixture was added iodomethane (0.19 mL), followed by stirring at room temperature for 15 minutes. To the reaction mixture were further added 60% sodium hydride (120 mg) and iodomethane (0.38 mL), followed by stirring at room temperature for 15 minutes. To the reaction mixture was added 1N aqueous hydrochloric acid solution under ice-cooling, followed by extraction with diethyl ether three times. The organic layer was dried and then concentrated to give tert-butyl-(9-methoxyspiro[5.5]undec-3-ylmethoxy)-dimethylsilane (393 mg) as a crude product.

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 15 minutes
  3. stirringby stirring at room temperature for 15 minutes
  4. temperaturecooling
  5. extractionfollowed by extraction with diethyl ether three times
  6. customThe organic layer was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-94e2c46928c748ef8f93946e6c9d65ad
Source dataset
uspto-grants-2012_10
Patent number
US08299296B2

Reaction notes

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