Triethylamine → HCID 14645565, compound

HRID 1722885Notes

Reaction equation

HRID 1722885 reaction equation
[Si:1]([O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([CH2:29][O:30][CH:31]=C1C3CC4CC(C[C-]1C4)C3)[CH:23]=[CH:22]2)([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.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(N(CC)CC)C.[Si](C1C=CC2C(=CC=CC=2)C=1C(OC)=[O:83])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C12CC3CC(CC(C3)C1=O)C2>C1COCC1>[Si:1]([O:18][C:19]1[CH:28]=[C:27]2[C:26](=[CH:21][CH:20]=1)[CH:25]=[C:24]([C:29]([O:30][CH3:31])=[O:83])[CH:23]=[CH:22]2)([C:14]([CH3:16])([CH3:15])[CH3:17])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 64151AdamantanoneHCID 19708423HCID 19708423, compoundHCID 21226445Aluminium lithium hydrideHCID 178455473HCID 178455473, compound

Product 1

HCID 14645565HCID 14645565, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

[(6-tert-Butyldiphenylsilyloxy-2-naphthyl)methoxymethylene]adamantane 1d). Approximately 7 g of a 2:1 mixture of TiCl3 and lithium aluminum hydride (Aldrich) was cautiously added to a 250 mL dry three-neck round bottom flask containing 150 mL of dry THF maintained at 0° C. by an ice bath. The resulting black mixture was stirred at 0° C. for 10 minutes and triethylamine (3.3 mL, 24 mmol) was added. The mixture was refluxed for 1 hour and a solution of methyl tert-butyldiphenylsilylnaphthoate (1.76 g, 4 mmol) and adamantanone (600 mg, 4 mmol) in 40 mL of dry THF was added over 6 hours. Reflux was continued for an additional 4 hours and the mixture cooled to room temperature.

Workup

  1. additionwas cautiously added to a 250 mL
  2. customdry three-neck round bottom flask
  3. additioncontaining 150 mL of dry THF
  4. temperatureThe mixture was refluxed for 1 hour
  5. temperatureReflux
  6. waitwas continued for an additional 4 hours
  7. temperaturethe mixture cooled to room temperature

Sources & evidence

ORD record
ord-2fd15f4c5388496bb9e8fd6391954f76
Source dataset
uspto-grants-1989_08
Patent number
US04857652

Reaction notes

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