tert-Butanol → HCID 86595724, compound

HRID 1178201Notes

Reaction equation

HRID 1178201 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:15]=[C:14]([C:16]3[S:17][CH:18]=[C:19]([CH2:21][OH:22])[N:20]=3)[CH:13]=[CH:12][N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.C(O)(C)(C)C.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:15]=[C:14]([C:16]3[S:17][CH:18]=[C:19]([CH:21]=[O:22])[N:20]=3)[CH:13]=[CH:12][N:11]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 159087TriacetoxyperiodinaneHCID 44590205HCID 44590205, compound

Product 1

HCID 86595724HCID 86595724, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7a (100 mg, 0.320 mmol) and 163 uL of t-butanol in 2 mL of DCM was added 163 mg of Dess_Martin periodinane reagent. The reaction mixture was stirred for 1 h after which it was quenched with sodium thiosulfate (1 mL). It was stirred until the two phase became clear. The organic layer was dried (Na2SO4) and concentrated in vacuo to give 35 mg (38%) the crude aldehyde 9a that was used directly for the next step. 1H NMR (CDCl3) δ 10.1 (s, 1H), 8.3 (d, 1H), 8.1 (s, 1H), 7.5 (d, 1H), 7.2 (s, 2H), 6.8 (s, 1H), 2.3 (s, 6H).

Workup

  1. customwas quenched with sodium thiosulfate (1 mL)
  2. stirringIt was stirred until the two phase
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-750e5a10e3a24ba5b0c37bfdd4dbba6e
Source dataset
uspto-grants-2007_10
Patent number
US07276502B2

Reaction notes

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