Isopropanol → HCID 12457581, compound

HRID 2197575Notes

Reaction equation

HRID 2197575 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[SH:6].[CH:7](O)([CH3:9])[CH3:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH:7]([S:6][C:2]1[S:1][CH:5]=[CH:4][N:3]=1)([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 178527881HCID 178527881, compound

Product 1

HCID 12457581HCID 12457581, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of thiazole-2-thiol (300 mg, 2.56 mmol), isopropanol (154 mg, 2.56 mmol) and triphenylphosphine (671.5 mg, 2.56 mmol) in THF (5 mL) was added DEAD (445.8 mg, 2.56 mmol) dropwise at room temperature. The mixture was stirred at room temperature for 3 hours. Reaction was completed according to t.l.c. The reaction mixture was allowed to stir over the weekend then concentrated and the residue was subjected to flash column chromatography using 10% ethyl acetate/hexane as solvent to give a colorless oil (260 mg, 64% yield).

Workup

  1. customReaction
  2. stirringto stir over the weekend
  3. concentrationthen concentrated

Sources & evidence

ORD record
ord-dd605e4c0c5a4273975b0100907692f4
Source dataset
uspto-grants-2012_12
Patent number
US08338604B2

Reaction notes

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