5-Fluoro-2-nitrophenol → HCID 86718459, compound

HRID 1396639Notes

Reaction equation

HRID 1396639 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@@H:16]([OH:17])[C@H:12]2[O:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:18][C:19]1[CH:20]=[CH:21][C:22]([N+:26]([O-:28])=[O:27])=[C:23](O)[CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[CH2:1]([O:8][C@@H:9]1[CH2:10][O:11][C@@H:12]2[C@@H:16]([O:17][C:21]3[CH:20]=[C:19]([F:18])[CH:24]=[CH:23][C:22]=3[N+:26]([O-:28])=[O:27])[CH2:15][O:14][C@H:13]12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 99375-Fluoro-2-nitrophenolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 58151011HCID 58151011, compound

Product 1

HCID 86718459HCID 86718459, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

To 6.0 g (25.2 mmol) (3R,3aR,6R,6aR)-6-benzyloxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol, 3.3 g (21 mmol) 5-fluoro-2-nitro-phenol and 8.3 g (31.5 mmol) triphenyl phosphine in 150 ml THF 7.3 g (31.5 mml) di-tert-butyl azodicarboxylate in 30 ml THF are added dropwise and the reaction mixture is stirred at 40° C. for 2 h. The reaction mixture is evaporated and the residue is purified by FC.

Workup

  1. customThe reaction mixture is evaporated
  2. customthe residue is purified by FC

Sources & evidence

ORD record
ord-ee73f7e49f004ffe84b87c38b19be19e
Source dataset
uspto-grants-2014_12
Patent number
US08901138B2

Reaction notes

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