p-Toluenesulfonic acid → HCID 19434053, compound

HRID 1736033Notes

Reaction equation

HRID 1736033 reaction equation
CO[C:3]([C:5]1[N:6]([CH2:16][CH2:17][CH2:18][CH2:19][OH:20])[S:7](=[O:15])(=[O:14])[C:8]2[S:13][CH:12]=[CH:11][C:9]=2[CH:10]=1)=[O:4].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH:32]([O:34][CH2:35][CH3:36])=[CH2:33].CC(C[AlH]CC(C)C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1>[CH2:32]([O:34][CH:35]([O:20][CH2:19][CH2:18][CH2:17][CH2:16][N:6]1[C:5]([CH2:3][OH:4])=[CH:10][C:9]2[CH:11]=[CH:12][S:13][C:8]=2[S:7]1(=[O:14])=[O:15])[CH3:36])[CH3:33]

Participants

7

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 8023Ethyl vinyl etherHCID 14487Diisobutylaluminum hydrideHCID 9855836Potassium sodium tartarateHCID 54079235HCID 54079235, compound

Product 1

HCID 19434053HCID 19434053, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Step B (1.01 g, 3.19 mmol) and p-toluenesulfonic acid (0.05 g) in anhydrous THF (30 mL) at 0° C. was added ethyl vinyl ether (0.5 mL, 5.23 mmol) and stirred for 15 min. To this solution was added via syringe DIBAL-H (1M solution in hexanes, 12 mmol); this mixture was stirred for 20 min at which point a solution of potassium sodium tartrate (8.0 g in 30 mL water) was added over 5 min. The resulting mixture was stirred overnight and extracted with ethyl acetate (2×50 mL). The combined extracts were dried (MgSO4) and evaporated to give an oil.

Workup

  1. additionwas added over 5 min
  2. stirringThe resulting mixture was stirred overnight
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customevaporated
  6. customto give an oil

Sources & evidence

ORD record
ord-37e16d473823413a98dd96f9ac8d512a
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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