Tetrahydrofuran → HCID 178520018, compound

HRID 1988204Notes

Reaction equation

HRID 1988204 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[SH:6][C:7]1[S:11][C:10]([C:12]([O:14]CC)=O)=[N:9][N:8]=1.[CH2:17]1[CH2:21]OC[CH2:18]1>>[CH:1]1([C:12]([CH:18]2[CH2:17][CH2:21]2)([C:10]2[S:11][C:7]([SH:6])=[N:8][N:9]=2)[OH:14])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 178418630HCID 178418630, compoundHCID 178470473Ethyl 5-sulfanyl-1,3,4-thiadiazole-2-carboxylate

Product 1

HCID 178520018HCID 178520018, compound

Procedure

To a solution of cyclopropylmagnesiumbromide (37 ml, 0.5 M/THF, 18.4 mmol at 0° C. was slowly added a THF solution of ethyl 5-mercapto-1,3,4-thiadiazole-2-carboxylate (1 g, 5.3 mmol). When half the solution was added, the cooling bath was removed and the rest of the solution was added. The mixture was stirred at room temperature for 4 hours then partitioned between aqueous NH4Cl and Et2O. The layers were separated and the aqueous phase was extracted with Et2O. The combined organic layers were washed with brine and dried over anhydrous Na2SO4. The solvent was evaporated and the residue chromatographed on silica gel (hexanes:acetone, 95:5) to give the title compound. 1H NMR (400 MHz, acetone-d6): 4.75 (s, 1H), 1.39-1.26 (m, 2H), 0.67-0.38 (m, 8H).

Workup

  1. additionWhen half the solution was added
  2. customthe cooling bath was removed
  3. additionthe rest of the solution was added
  4. customthen partitioned between aqueous NH4Cl and Et2O
  5. customThe layers were separated
  6. extractionthe aqueous phase was extracted with Et2O
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over anhydrous Na2SO4
  9. customThe solvent was evaporated
  10. customthe residue chromatographed on silica gel (hexanes:acetone, 95:5)

Sources & evidence

ORD record
ord-5ac645a00eec4642bf3c28ae97b8fabd
Source dataset
uspto-grants-2009_06
Patent number
US07553973B2

Reaction notes

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