Water → HCID 54447813, compound

HRID 1735856Notes

Reaction equation

HRID 1735856 reaction equation
[CH2:1]([C:4]1([CH:19]=[CH:20][C:21](OC)=[O:22])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)[CH:2]=[CH2:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH2:1]([C:4]1([CH:19]=[CH:20][CH2:21][OH:22])[C:5]2[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=2[CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 53825216HCID 53825216, compound

Product 1

HCID 54447813HCID 54447813, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolved methyl 3-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-propenoate (6.00 g, 0.0188 mol) in 80 mL of dry THF. Cooled to 0° C. under a nitrogen atmosphere, and added lithium aluminum hydride (18.8 mL of 1.0M in THF, 0.018 mol) via syringe. Warmed slowly to room temperature and stirred for 20 hours. Recooled to 0° C., and carefully added 0.8 mL water, 0.8 mL of 1N NaOH, and then 2.5 mL of water in sequence. Stirred at room temperature for 1 hour, and filtered through celite. Washed filtrate with saturated NH4Cl, dried with MgSO4, filtered, and evaporated. Purified crude product by flash chromatography on silica gel eluting with 1:4 ethyl acetate:hexane then 1:2 ethyl acetate:hexane. Combined appropriate fractions, and evaporated to give 4.87 g (89% yield) of 3-[10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-yl]-prop-2-en-1-ol as a colorless oil.

Workup

  1. temperatureWarmed slowly to room temperature
  2. customRecooled to 0° C.
  3. stirringStirred at room temperature for 1 hour
  4. filtrationfiltered through celite
  5. dry with materialWashed filtrate with saturated NH4Cl, dried with MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customPurified crude product by flash chromatography on silica gel eluting with 1:4 ethyl acetate
  9. customevaporated

Sources & evidence

ORD record
ord-dcb8d0e4b873418fb35046e4de3b4ed0
Source dataset
uspto-grants-1996_07
Patent number
US05538986

Reaction notes

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