Aluminium lithium hydride → HCID 21941348, compound

HRID 1158880Notes

Reaction equation

HRID 1158880 reaction equation
C([O:3][C:4]([C:6]1[S:14][C:13]2[CH2:12][CH2:11][S:10][CH2:9][C:8]=2[CH:7]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.C(Cl)Cl.[O-2].[O-2].[Mn+4]>[S:14]1[C:13]2[CH2:12][CH2:11][S:10][CH2:9][C:8]=2[CH:7]=[C:6]1[CH:4]=[O:3]

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68443083HCID 68443083, compound

Product 1

HCID 21941348HCID 21941348, compoundYield 36.2%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 178418406HCID 178418406, compoundSolvent

Procedure

The 1.1 gram (4.8 mmol) 6,7-Dihydro-4H-thieno[3,2-c]thiopyran-2-carboxylic acid ethyl ester was dissolved in 100 ml THF and LAH (40 ml, 0.5M in DMG) was injected and the reaction was left at 23° C. for 10 minutes. Then it was refluxed for 18 hrs. Quenched at 23° C. with water (10 ml). The organic layer decanted and the remaining was washed with 20 ml DCM. The combined organic layers dried over sodium sulfate. Filter, concentrate and flash column chromatograph with 10-20% ethyl acetate produced 940 mg crude product. This crude material was dissolved in DCM (40 ml) and manganese dioxide (2 gram was added). The reaction was carried on at 23° C. for half an hour. The material was then filtered through a pad of celite concentrated. Flash column chromatography gave 320 mg (36%) product.

Workup

  1. temperatureThen it was refluxed for 18 hrs
  2. customQuenched at 23° C. with water (10 ml)
  3. customThe organic layer decanted
  4. washthe remaining was washed with 20 ml DCM
  5. dry with materialThe combined organic layers dried over sodium sulfate
  6. filtrationFilter
  7. concentrationconcentrate
  8. customflash column chromatograph with 10-20% ethyl acetate produced 940 mg crude product
  9. waitThe reaction was carried on at 23° C. for half an hour
  10. filtrationThe material was then filtered through a pad of celite
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-7f1b903a2a0d433ba6ff4e0a0545f06e
Source dataset
uspto-grants-2010_10
Patent number
US07812014B2

Reaction notes

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