3-Methoxyphenol → HCID 66605942, compound

HRID 1408307Notes

Reaction equation

HRID 1408307 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](O)[CH:6]=[CH:7][CH:8]=1.[CH2:10]([OH:16])[CH2:11][CH2:12][CH2:13][CH:14]=[CH2:15].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:10]([O:16][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1)[CH2:11][CH2:12][CH2:13][CH:14]=[CH2:15]

Participants

6

Reactant 4

HCID 90073-MethoxyphenolHCID 11776TriphenylphosphineHCID 699635-Hexen-1-olHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 66605942HCID 66605942, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3-methoxy phenol (1.24 g, 10 mmol), 5-hexen-1-ol, 4a (1.4 mL, 12 mmol) and Ph3P (3.14 g, 12 mmol) in THF (20 mL) at 0° C. was added diisopropylazodicarboxylate (2.3 mL, 12 mmol) dropwise. After stirring the solution for 30 min at 0° C. the reaction mixture was warmed to 23° C. and stirred for 3 h. The reaction mixture was concentrated in vacuo and the residue was subjected to column chromatography (98:2 hexanes:EtOAc) to yield 1.98 g of 5a (96% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 1.58-1.66 (m, 2H), 1.80-1.88 (m, 2H), 2.15-2.20 (m, 2H), 3.82 (s, 3H), 3.98 (t, J=6.4 Hz, 2H), 5.02-5.12 (m, 2H), 5.83-5.92 (m, 1H), 6.52-6.56 (m, 3H), 7.19-7.24 (m, 1H); 13C NMR (100 MHz, CDCl3): δ 25.3, 28.7, 33.4, 55.1, 67.6, 100.9, 106.0, 106.6, 114.7, 129.8, 138.5, 160.3, 160.8; FT-IR (film, NaCl) νmax=3075, 2939, 1599, 1493, 1287, 1200, 1152, 1046 cm−1; CI LRMS m/z (ion): 207.25 (M+H)+.

Workup

  1. temperaturewas warmed to 23° C.
  2. stirringstirred for 3 h
  3. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-802174f481ea403dbe4609a34aa31b7c
Source dataset
uspto-grants-2014_12
Patent number
US08921349B2

Reaction notes

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