4-Fluorophenol → HCID 9913245, compound

HRID 916693Notes

Reaction equation

HRID 916693 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[OH:15][CH2:16][C:17]1[CH:21]=[C:20]([C:22]2[CH:23]=[C:24]([C:28]([NH:31][S:32]([CH2:35][C:36]([F:39])([F:38])[F:37])(=[O:34])=[O:33])([CH3:30])[CH3:29])[CH:25]=[CH:26][CH:27]=2)[N:19]([CH3:40])[N:18]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[F:60][C:61]1[CH:66]=[CH:65][C:64](O)=[CH:63][CH:62]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[F:37][C:36]([F:39])([F:38])[CH2:35][S:32]([NH:31][C:28]([C:24]1[CH:25]=[CH:26][CH:27]=[C:22]([C:20]2[N:19]([CH3:40])[N:18]=[C:17]([CH2:16][O:15][C:64]3[CH:65]=[CH:66][C:61]([F:60])=[CH:62][CH:63]=3)[CH:21]=2)[CH:23]=1)([CH3:30])[CH3:29])(=[O:34])=[O:33]

Participants

7

Reactant 5

HCID 97324-Fluorophenol2×HCID 11776Triphenylphosphine2×HCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 5363146Diisopropyl azodicarboxylateHCID 58757355HCID 58757355, compound

Product 1

HCID 9913245HCID 9913245, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (57 mg, 0.27 mmol) was added dropwise to a stirred solution of the alcohol from Step 5 (75 mg, 0.19 mmol), PPh3 (75 mg, 0.27 mmol) and 4-fluorophenol (26 mg, 0.23 mmol) in THF (10 mL) under N2 and the resulting mixture was stirred at RT for 2 hours. Further DIAD (19 mg, 0.09 mmol), PPh3 (25 mg, 0.09 mmol) and 4-fluorophenol (11 mg, 0.09 mmol) were added and stirring was continued for a further 30 min. The reaction mixture was then concentrated under reduced pressure while loading on to MgSO4 and then purified by column chromatography on silica eluting with 100% Et2O to yield the desired ether (19 mg, 20%). 1H NMR (CDCl3, 360 MHz) δ 7.58-7.53 (2H, s), 7.49 (1H, t, J=7.5 Hz), 7.37 (1H, d, J=7.5 Hz), 6.97 (4H, app. d, J=6.1 Hz), 6.41 (1H, s), 5.05 (2H, s), 4.99 (1H, s), 3.88 (3H, s), 3.48 (2H, q, J=8.9 Hz), 1.81 (6H, s). MS (ES+) C22H23F4N3O3S requires: 485, found: 486 (M+H+, 100%).

Workup

  1. stirringstirring
  2. waitwas continued for a further 30 min
  3. concentrationThe reaction mixture was then concentrated under reduced pressure while loading on to MgSO4
  4. custompurified by column chromatography on silica eluting with 100% Et2O
  5. customto yield the desired ether (19 mg, 20%)

Sources & evidence

ORD record
ord-5bd51d4a0f644fe3afd8b9319cd7d943
Source dataset
uspto-grants-2007_09
Patent number
US07271191B2

Reaction notes

Loading…