Water → HCID 23372177, compound

HRID 1900244Notes

Reaction equation

HRID 1900244 reaction equation
[CH:1]1[C:11]2[CH:10]([CH:12]([CH2:17][CH:18]=[CH2:19])[C:13](OC)=[O:14])[C:9]3[CH:20]=[CH:21][CH:22]=[CH:23][C:8]=3[CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH:1]1[C:11]2[CH:10]([CH:12]([CH2:17][CH:18]=[CH2:19])[CH2:13][OH:14])[C:9]3[CH:20]=[CH:21][CH:22]=[CH:23][C:8]=3[CH2:7][O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23372179HCID 23372179, compound

Product 1

HCID 23372177HCID 23372177, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolved methyl 2-[6, 11-dihydro-dibenzo[b,e]oxepin-11-yl]-pent-4-enoate (9.00 g, 0.0292 mol) in 100 mL of dry THF, and cooled to 0° C. under a nitrogen atmosphere. Added 1.0M lithium aluminum hydride in THF (29.2 mL, 0.0292 mol) via addition funnel. Stirred at room temperature for 45 mins. Added 1 mL of water, 1 mL of 1N NaOH, then 3 mL of water. Stirred at room temperature for 30 mins. then filtered through celite. Washed celite cake with ethyl acetate. Washed filtrate with saturated NaCl, dried with MgSO4, filtered, and evaporated. Purified crude product by flash chromatography on silica gel eluting with 10% ethyl acetate-hexane then 25% ethyl acetate-hexane. Combined appropriate fractions and evaporated to give 6.78 g (83% yield) of 2-[6,11-dihydro-dibenzo[b,e]oxepin-11-yl]-pent-4-en-1-ol.

Workup

  1. additionvia addition funnel
  2. stirringStirred at room temperature for 30 mins
  3. filtrationthen filtered through celite
  4. washWashed celite cake with ethyl acetate
  5. dry with materialWashed filtrate with saturated NaCl, dried with MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customPurified crude product by flash chromatography on silica gel eluting with 10% ethyl acetate-hexane
  9. customevaporated

Sources & evidence

ORD record
ord-ef6e6eed553f407b924878537d7223ff
Source dataset
uspto-grants-1996_11
Patent number
US05574173

Reaction notes

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