Sodium borohydride → HCID 59770152, compound

HRID 2218637Notes

Reaction equation

HRID 2218637 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[CH:19]=[O:20])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CCO>[CH:12]1[C:8]2[CH2:9][CH2:10][C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[C:6](=[CH:16][C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[CH2:19][OH:20])[C:7]=2[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59770421HCID 59770421, compound

Product 1

HCID 59770152HCID 59770152, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Treat a solution of 2-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-benzaldehyde (125 mg, 0.4 mmol) in EtOH (4 mL) with NaBH4 (30 mg, 0.8 mmol). After 4 h at room temperature, quench the reaction with 1N HCl and concentrate. Shake the residue en with water/EtOAc. Dry the organic layer (MgSO4) and concentrate to give 130 mg crude product. Purify on silica gel (EtOAc/hexane) to give 90 mg (72%) colorless oil which slowly crystallized, mp 121.8° C. 1H NMR (CDCl3) δ 3.28 (br s, 4H), 4.85 (s, 2H), 6.77-7.60 (m, 13H; MS (EI) 312. HPLC shows 98% purity.

Workup

  1. customquench
  2. customthe reaction with 1N HCl
  3. concentrationconcentrate
  4. dry with materialDry the organic layer (MgSO4)
  5. concentrationconcentrate
  6. customto give 130 mg crude product
  7. customPurify on silica gel (EtOAc/hexane)

Sources & evidence

ORD record
ord-2a288beada2f46d1b5aabe253139fe81
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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