Hydrochloric Acid → HCID 86721376, compound

HRID 869619Notes

Reaction equation

HRID 869619 reaction equation
[C:1]([C:3](=[C:5]1[C:11]2[CH:12]=[CH:13][C:14]([C:16](OCCC)=[O:17])=[CH:15][C:10]=2[CH2:9][O:8][C:7]2[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:6]1=2)[CH3:4])#[N:2].[BH4-].[Li+].Cl>C1COCC1>[F:26][C:23]1[CH:24]=[CH:25][C:6]2=[C:7]([CH:22]=1)[O:8][CH2:9][C:10]1[CH:15]=[C:14]([CH2:16][OH:17])[CH:13]=[CH:12][C:11]=1/[C:5]/2=[C:3](/[CH3:4])\[C:1]#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 86721486HCID 86721486, compound

Product 1

HCID 86721376HCID 86721376, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

[step 5] Propyl 11-(1-cyanoethylidene)-3-fluoro-6,11-dihydrodibenzo[b,e]oxepin-8-carboxylate (15.5 g, 44.1 mmol, E/Z=1/1) obtained in step 4 was dissolved in THF (220 mL), lithium borohydride (4.8 g, 221 mmol) was added, and the mixture was stirred at 60° C. for 3 hr. Under ice-cooling, the mixture was added dropwise to 2 mol/L hydrochloric acid, and the mixture was extracted 3 times with chloroform (550 mL). The combined organic layers were dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified 3 times by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-40/60 v/v) to give (E)-2-[3-fluoro-8-(hydroxymethyl)dibenzo[b,e]oxepin-11(6H)-ylidene]propanenitrile (6.06 g, 47%).

Workup

  1. temperatureUnder ice-cooling
  2. extractionthe mixture was extracted 3 times with chloroform (550 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified 3 times by silica gel column chromatography (hexane/ethyl acetate=100/0 v/v-40/60 v/v)

Sources & evidence

ORD record
ord-141ae4dc0ed146629aa577764aae3c52
Source dataset
uspto-grants-2015_03
Patent number
US08969345B2

Reaction notes

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