Acetic Acid → HCID 68334859, compound

HRID 2371021Notes

Reaction equation

HRID 2371021 reaction equation
[S:1]1[C:9]2[CH2:8][CH2:7][O:6][CH:5]([CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:4]=2[CH:3]=[CH:2]1.C1C(=O)N([I:26])C(=O)C1.CC(O)=O.C(N(CC)CC)C>C(Cl)(Cl)Cl>[I:26][C:2]1[S:1][C:9]2[CH2:8][CH2:7][O:6][CH:5]([CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 120273N-IodosuccinimideHCID 68334996HCID 68334996, compound

Product 1

HCID 68334859HCID 68334859, compoundYield 583.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of tert-butyl (6,7-dihydro-4H-thieno[3,2-c]pyran-4-yl)methylcarbamate (2.9 g, 1.3 mmol, 1 eq), NIS (5.2 g, 2.2 mmol, 2 eq), and AcOH (3 mL) in CHCl3 (50 mL) was stirred at room temperature for 7 hr. The reaction mixture was neutralized with triethyl amine, concentrated, and diluted with water. The mixture was extracted with n-hexane. The organic phase was dried over Na2SO4, concentrated, and purified by column chromatography to give the desired product (3 g).

Workup

  1. concentrationconcentrated
  2. additiondiluted with water
  3. extractionThe mixture was extracted with n-hexane
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-b56e7c99678542008a394f2280599d17
Source dataset
uspto-grants-2014_04
Patent number
US08710245B2

Reaction notes

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