Lithium borohydride → HCID 69235485, compound

HRID 1593644Notes

Reaction equation

HRID 1593644 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9]3[CH2:11][CH2:12][CH:13]([C:15](OCC)=[O:16])[CH2:14][C:8]=3[C:7]=2[CH:20]=1)#[N:2].[Li+].[BH4-]>C1COCC1>[OH:16][CH2:15][CH:13]1[CH2:14][C:8]2[C:7]3[CH:20]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=3[S:10][C:9]=2[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 69232624HCID 69232624, compound

Product 1

HCID 69235485HCID 69235485, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a room temperature solution of ethyl 8-cyano-1,2,3,4-tetrahydrodibenzo[b,d]thiophene-2-carboxylate (0.72 g, 2.53 mmol) in THF (4 mL) was added LiBH4 (6.33 mL of 2 N solution in THF, 12.66 mmol). The reaction was heated at reflux for 5.5 hour, then was cooled in ice water, and quenched with 7 mL of 1 N NaOH (aq) solution. After stirring for a few minutes at room temperature, the mixture was extracted with EtOAc. The organic layer was washed with water, then brine, then was dried over MgSO4, filtered, and concentrated. Purification by chromatography on silica gel (50% EtOAc in hexane) afforded 0.24 g (39%) of the title compound as a white solid: mp 165-166° C.; MS (ES) m/z=243 [M]+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 5.5 hour
  3. customquenched with 7 mL of 1 N NaOH (aq) solution
  4. extractionthe mixture was extracted with EtOAc
  5. washThe organic layer was washed with water
  6. dry with materialbrine, then was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by chromatography on silica gel (50% EtOAc in hexane)

Sources & evidence

ORD record
ord-357496e59da94d5998b5dc04e9bb30dd
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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