Diethyl Ether → HCID 18794596, compound

HRID 1004442Notes

Reaction equation

HRID 1004442 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)[C:11]2[CH:10]=C[CH:8]=[CH:7][C:6]1=2)=O.[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[C:31](=NN)[CH:30]([CH2:37][CH2:38][N:39]1[CH2:44][CH2:43][CH:42]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH2:41][CH2:40]1)[CH2:29][CH2:28]2.CC[O:53]CC.CCOC(C)=O.CCCCCC.[CH2:68]([Cl:70])Cl>>[Cl:70][C:68]1[CH:8]=[CH:7][C:6]([CH2:23][O:24][C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[C:31](=[O:53])[CH:30]([CH2:37][CH2:38][N:39]2[CH2:44][CH2:43][CH:42]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[CH2:41][CH2:40]2)[CH2:29][CH2:28]3)=[CH:11][CH:10]=1

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 159087TriacetoxyperiodinaneHCID 21226206Ethyl acetate hexaneHCID 57303657HCID 57303657, compound

Product 1

HCID 18794596HCID 18794596, compound

Procedure

Dess-Martin reagent (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one, 3.0 g, 4.8 mmol) was added to a solution of the title D compound 3 (1.1 g, 3.2 mmol) in CH2Cl2 (20 mL) stirring under argon at ambient temperature in a flame-dried flask. After stirring at ambient temperature for 1.8 hours, ether was added and the reaction evaporated in vacuo. The residue was transferred to a separatory funnel with ether (200 mL) and 1/1 10% Na2S2O3 /saturated NaHCO3 (150 mL). Extraction with ether and washing with water (50 mL) and brine (50 mL) and drying over MgSO4 afforded 1.1 g of crude product. Flash chromatography (silica gel, 10% EtOAc/hexane) afforded 0.80 g (72%) yield of compound 6: Rf (silica, 15% EtOAc/hexane)=0.45.

Workup

  1. stirringAfter stirring at ambient temperature for 1.8 hours
  2. customthe reaction evaporated in vacuo
  3. customThe residue was transferred to a separatory funnel with ether (200 mL) and 1/1 10% Na2S2O3 /saturated NaHCO3 (150 mL)
  4. extractionExtraction with ether
  5. washwashing with water (50 mL) and brine (50 mL)
  6. dry with materialdrying over MgSO4
  7. customafforded 1.1 g of crude product

Sources & evidence

ORD record
ord-e4d7da6b782648969ff02ea5e450187f
Source dataset
uspto-grants-2000_04
Patent number
US06048877

Reaction notes

Loading…