Hydrochloric Acid → HCID 22467310, compound

HRID 1934558Notes

Reaction equation

HRID 1934558 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Si:7]([O:24][C:25]1[C:30]2[CH2:31][CH2:32][CH2:33][CH:34]([C:36](OC)=[O:37])[CH2:35][C:29]=2[CH:28]=[CH:27][CH:26]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>C1COCC1>[Si:7]([O:24][C:25]1[C:30]2[CH2:31][CH2:32][CH2:33][CH:34]([CH2:36][OH:37])[CH2:35][C:29]=2[CH:28]=[CH:27][CH:26]=1)([C:20]([CH3:21])([CH3:22])[CH3:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 22467320HCID 22467320, compound

Product 1

HCID 22467310HCID 22467310, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (66 mg) in THF (20 ml) was added dropwise a solution of methyl 1-(tert-butyldiphenylsilyloxy)-6,7,8,9-tetrahydro-5H- benzocycloheptene -6-carboxylate (800 mg) in THF (4 ml) at 5° C. The mixture was stirred at the same temperature for 1 hour and then at room temperature for 30 minutes. The mixture was added with 1N-hydrochloric acid 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 2:1) to give [1-(tert-butyldiphenylsilyloxy)-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl]methanol (715 mg) as an oil.

Workup

  1. waitat room temperature for 30 minutes
  2. extractionextracted 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 2:1)

Sources & evidence

ORD record
ord-da912aeac15e48b2be9fa1e8097ce658
Source dataset
uspto-grants-2002_05
Patent number
US06384072B1

Reaction notes

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