Diethyl Ether → HCID 86698152, compound

HRID 1424500Notes

Reaction equation

HRID 1424500 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]=[C:9]([CH2:16][N:17]3[C:21]4[CH:22]=[N:23][CH:24]=[CH:25][C:20]=4[N:19]([CH:26]4[CH2:28][CH2:27]4)[C:18]3=[O:29])[N:10]([CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[C:5]2=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(OCC)C>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]=[C:9]([CH2:16][N:17]3[C:21]4[CH:22]=[N:23][CH:24]=[CH:25][C:20]=4[N:19]([CH:26]4[CH2:28][CH2:27]4)[C:18]3=[O:29])[N:10]([CH2:11][CH2:12][CH2:13][CH:14]=[O:15])[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 159087TriacetoxyperiodinaneHCID 86698149HCID 86698149, compound

Product 1

HCID 86698152HCID 86698152, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the alcohol 14 (5 g, 12.11 mmoles) dissolved in DCM (80 mL) was added dess-martin periodinane (6.934 g, 1.35 eq, CAS 87413-09-0). The resulting mixture was stirred at Rt overnight. Diethylether was added (150 mL) and the mixture was stirred for 15 minutes. The mixture was filtrated and the filtrate washed quickly with an aqueous Na2S2O3 solution, dried on Na2SO4, filtrated and evaporated. The resulting solid was washed again with a solution of 5% methanol in dichloromethane and the filtrate was washed with a Na2S2O3 solution and dried over Na2SO4. The solution was concentrated and the aldehyde 67-1 was obtained as a light yellow solid (4.6 g, 93% yield) and was used as such in the next step. LCMS m/z=411 (M+H)+

Workup

  1. stirringthe mixture was stirred for 15 minutes
  2. filtrationThe mixture was filtrated
  3. washthe filtrate washed quickly with an aqueous Na2S2O3 solution
  4. customdried on Na2SO4
  5. filtrationfiltrated
  6. customevaporated
  7. washThe resulting solid was washed again with a solution of 5% methanol in dichloromethane
  8. washthe filtrate was washed with a Na2S2O3 solution
  9. dry with materialdried over Na2SO4
  10. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-330203f73381438ba0dd9d078c0a7907
Source dataset
uspto-grants-2015_01
Patent number
US08927720B2

Reaction notes

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