Acetaldehyde → HCID 13800139, compound

HRID 1906870Notes

Reaction equation

HRID 1906870 reaction equation
[OH:1][CH:2]1[CH:8]([OH:9])[C:7]2[CH:10]=[C:11]([F:14])[CH:12]=[CH:13][C:6]=2[NH:5][CH2:4][CH2:3]1.[CH:15](=O)[CH3:16].[CH2:18](OC(OCC)C)[CH3:19].C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.B(F)(F)F.CCOCC>[F:14][C:11]1[CH:12]=[CH:13][C:6]2[N:5]3[CH2:18][CH2:19][C:2]4([O:1][CH:15]([CH3:16])[O:9][CH:8]4[C:7]=2[CH:10]=1)[CH2:3][CH2:4]3

Participants

8

Reactant 5

HCID 177AcetaldehydeHCID 7765AcetalHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 57224144HCID 57224144, compound

Product 1

HCID 13800139HCID 13800139, compound

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.7 g of 1,4-ethano-b 4,5-dihydroxy-7-fluoro-2,3,4,5-tetrahydro-1H-1-benzazepine in 50 ml of dry tetrahydrofuran, 2.2 ml of boron trifluoride etherate was added dropwise, with stirring, at room temperature, under nitrogen. To the mixture, 5 ml of acetaldehyde was added. After stirring for ca. 16 hrs, 1.2 ml of freshly distilled boron trifluoride etherate and of ca. 2 ml of acetaldehyde diethylacetal were added, and the solution was stirred for ca. two hrs at 40° C. The reaction mixture was then stirred into a mixture of 200 ml of saturated sodium bicarbonate solution and a few ml of saturated potassium carbonate solution. Extraction with ethyl ether (twice) and ethyl acetate, washing of the combined organic extracts with brine, drying over anhydrous potassium carbonate and evaporation of the solvent provided 4.8 g of a semi-solid. Purification by means of flash chromatography (silica gel, 1-3% methanol-dichloromethane) followed by recrystallization from hexane-diisopropyl ether gave 1.8 g (44%) of product, mp 103°- 107° C.

Workup

  1. stirringAfter stirring for ca. 16 hrs
  2. stirringthe solution was stirred for ca. two hrs at 40° C
  3. extractionExtraction with ethyl ether (twice) and ethyl acetate
  4. washwashing of the combined organic extracts with brine
  5. dry with materialdrying over anhydrous potassium carbonate and evaporation of the solvent

Sources & evidence

ORD record
ord-18d84ae7bfe54bba97722ebb111055d4
Source dataset
uspto-grants-1987_03
Patent number
US04654336

Reaction notes

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