Trifluoroacetic acid → HCID 86607647, compound

HRID 1593645Notes

Reaction equation

HRID 1593645 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:17][C:7]2[C:8]3[CH:14]=[C:13]([C:15]#[N:16])[CH:12]=[CH:11][C:9]=3[S:10][C:6]=2[CH2:5][CH2:4]1.C(O)(C(F)(F)F)=O.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl.CCOC(C)=O>[CH:2]([CH:3]1[CH2:17][C:7]2[C:8]3[CH:14]=[C:13]([C:15]#[N:16])[CH:12]=[CH:11][C:9]=3[S:10][C:6]=2[CH2:5][CH2:4]1)=[O:1]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 69235485HCID 69235485, compound

Product 1

HCID 86607647HCID 86607647, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a room temperature suspension of 8-(hydroxymethyl)-6,7,8,9-tetrahydrodibenzo[b,d]thiophene-2-carbonitrile (0.24 g, 1 mmol) in 4 mL CH2Cl2 was added TFA (0.5 mL). To the resulting homogeneous solution was added Dess-Martin periodinane (0.243 g, 1 mmol). Precipitates were formed after reaction mixture was stirred for 10 minutes. The resulting suspension was cooled in ice water, and diluted with EtOAc (15 mL), then was treated with 10 mL of 1.25 N NaOH (aq.) solution. After stirring for a few minutes, the organic layer was collected, washed with water, then brine, then was dried over MgSO4), filtered, and concentrated. Purification by chromatography on silica gel (25% EtOAc in hexane) afforded 0.14 g (58%) of the title compound as a white solid: mp 172-173° C.; MS (ES) m/z=241 [M]+.

Workup

  1. customPrecipitates
  2. customwere formed
  3. customafter reaction mixture
  4. stirringAfter stirring for a few minutes
  5. customthe organic layer was collected
  6. washwashed with water
  7. dry with materialbrine, then was dried over MgSO4),
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by chromatography on silica gel (25% EtOAc in hexane)

Sources & evidence

ORD record
ord-3b3b2f7685a74d8cb1129358a7434679
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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