Tetrahydrofuran → HCID 86625163, compound

HRID 1663399Notes

Reaction equation

HRID 1663399 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:11])[C:9]=1[OH:10])[CH:5]=[O:6].[N:12]([C:20](OC(C)C)=O)=NC(OC(C)C)=O.[C:26]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:45]1[CH2:49]O[CH2:47][CH2:46]1>>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:11])[C:9]=1[O:10][CH2:47][C:46]1[CH:26]=[N:12][CH:20]=[CH:49][CH:45]=1)[CH:5]=[O:6]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 854055-Bromo-3,4-dihydroxybenzaldehyde

Product 1

HCID 86625163HCID 86625163, compound

Procedure

A mixture of 3-bromo-4,5-dihydroxy-benzaldehyde (1 g), 3-pyridinecarbinol (448 μl), diisopropyl azodicarboxylate (DIAD) (908 μl) and polymer supported triphenylphosphine (1.53 g, 3 mmol/g loading) in THF (50 ml) was stirred under a nitrogen atmosphere for 17 h. The mixture was filtered, diluted with ethyl acetate and washed with water. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silicagel in heptane/ethyl acetate 1/0→0/1 (v/v) as eluent.

Workup

  1. filtrationThe mixture was filtered
  2. additiondiluted with ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silicagel in heptane/ethyl acetate 1/0→0/1 (v/v) as eluent

Sources & evidence

ORD record
ord-9044ce5a420640819d45cf9db907a057
Source dataset
uspto-grants-2011_10
Patent number
US08034945B2

Reaction notes

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