Diethyl Ether → HCID 86698154, compound

HRID 1424502Notes

Reaction equation

HRID 1424502 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]=[C:9]([CH2:17][N:18]3[C:22]4[CH:23]=[N:24][CH:25]=[CH:26][C:21]=4[N:20]([CH:27]4[CH2:29][CH2:28]4)[C:19]3=[O:30])[N:10]([CH2:11][CH2:12][CH2:13][CH:14]([OH:16])[CH3:15])[C:5]2=[CH:4][CH:3]=1.[CH3:31]C(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]([CH2:17][N:18]3[C:22]4[CH:23]=[N:24][CH:25]=[CH:26][C:21]=4[N:20]([CH:27]4[CH2:29][CH2:28]4)[C:19]3=[O:30])[N:10]([CH2:11][CH2:12][CH2:13][C:14]([OH:16])([CH3:31])[CH3:15])[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 159087TriacetoxyperiodinaneHCID 86698153HCID 86698153, compound

Product 1

HCID 86698154HCID 86698154, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the alcohol 67 (380 mg, 0.89 mmoles) dissolved in DCM (30 mL) was added dess-martin periodinane (509 mg, 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 purified by flash chromatography (10% MeOH in DCM) and the aldehyde 75 was obtained as a light yellow solid (218 mg, 58% yield). LCMS m/z=425 (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. customThe resulting solid was purified by flash chromatography (10% MeOH in DCM)

Sources & evidence

ORD record
ord-5a7a7af366494c71ab1b89996a7c77e2
Source dataset
uspto-grants-2015_01
Patent number
US08927720B2

Reaction notes

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