Hydrochloric Acid → HCID 18663597, compound

HRID 1956571Notes

Reaction equation

HRID 1956571 reaction equation
CN1CCOCC1.ClC(OCC(C)C)=O.[Cl:16][C:17]1[C:27]2[CH:26]=[C:25]([C:28](O)=[O:29])[C:24]3[CH:31]=[CH:32][CH:33]=[CH:34][C:23]=3[O:22][C:21]=2[CH:20]=[CH:19][CH:18]=1.[BH4-].[Na+].Cl.[OH-].[Na+]>C(COC)OC.O>[Cl:16][C:17]1[C:27]2[CH:26]=[C:25]([CH2:28][OH:29])[C:24]3[CH:31]=[CH:32][CH:33]=[CH:34][C:23]=3[O:22][C:21]=2[CH:20]=[CH:19][CH:18]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 14798Sodium HydroxideHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 18663598HCID 18663598, compound

Product 1

HCID 18663597HCID 18663597, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
-15 °C

Procedure

2.0 ml (18.33 mmol) of N-methylmorpholine and 2.4 ml (18.33 mmol) of isobutyl chloroformate are added dropwise at -15° C. to a solution of 5.0 g (18.33 mmol) of 1-chloro-dibenz[b,f]oxepine-10-carboxylic acid in dimethoxyethane. After 5 minutes filtration is carried out and at -15° C. a solution of 1.39 g (36.67 mmol) of sodium borohydride in 15 ml of water is added dropwise to the filtrate. The mixture is stirred for 15 minutes at -15° C., then 35 ml of 1N hydrochloric acid are added and the mixture is allowed to warm to room temperature. The reaction mixture is rendered basic with sodium hydroxide and extracted 4× with ethyl acetate. The organic phase is washed 1× with water, dried over sodium sulfate and concentrated. 4.58 g (17.7 mmol)=96.6% of crude (1-chlorodibenz[b,f]oxepin-10-yl)-methanol are obtained in the form of a yellow oil; TLC (silica gel; ethyl acetate/hexane=1:1; UV): Rf =10.46; 1H-NMR (CDCl3, 200 MHz): 2.42 (sbr, 1H); 1H); 4.71 (s, 2H); 7.10-7.45 (m, 7H).

Workup

  1. filtrationAfter 5 minutes filtration
  2. customis carried out and at -15° C.
  3. additionis added dropwise to the filtrate
  4. temperatureto warm to room temperature
  5. extractionextracted 4× with ethyl acetate
  6. washThe organic phase is washed 1× with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-197ec3caf0464b2e8a91c676b4a37b3e
Source dataset
uspto-grants-1998_07
Patent number
US05780500

Reaction notes

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