4-Butoxybenzaldehyde → HCID 68619133, compound

HRID 2373144Notes

Reaction equation

HRID 2373144 reaction equation
[CH2:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[Br:14][C:15]1[CH:20]=[C:19]([CH2:21]P(OCC)(=O)OCC)[CH:18]=[CH:17][C:16]=1[CH2:30]P(OCC)(=O)OCC.[CH3:39][C:40]([O-:43])(C)[CH3:41].[K+]>C1COCC1>[Br:14][C:15]1[CH:20]=[C:19](/[CH:21]=[CH:10]/[C:9]2[CH:12]=[CH:13][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:7][CH:8]=2)[CH:18]=[CH:17][C:16]=1/[CH:30]=[CH:12]/[C:9]1[CH:10]=[CH:41][C:40]([O:43][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:39][CH:8]=1

Participants

5

Reactant 3

HCID 798134-ButoxybenzaldehydeHCID 10678162HCID 10678162, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 68619133HCID 68619133, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of p-butoxybenzaldehyde (71) (2.0 g, 11.2 mmol) and tetraethyl 2-bromo-α,α′-p-xylenebisphosphonate (70) (2.55 g,. 5.5 mmol) in dry THF (70 ml) at 0° C. was added 12 ml of 1 M solution of KOtBu in THF. After 2 hours the reaction was quenched by addition of 70 ml of methanol. A light yellow solid was collected by filtration and washed three times with methanol to afford NMR-pure product in 2.36 g (84.5%) yield.1H NMR (CDCl3, 500 MHz) δppm: 7.70 (s, 1H), 7.62 (d, J=8.5 Hz, 1H), 7.47 (d, J=8.0 Hz, 2H), 7.44 (d, J=8.5 Hz, 2H), 7.4 (d, J=7.5 Hz, 1H), 7.32 (d, J=16.5 Hz, 1H, ═CH), 7.06 (d, J=16.5 Hz, 1H, ═C), 7.01 (d, J=16.0 Hz, 1H, ═CH), 6.85-6.95 (m, 5H, 4 Ar—H, 1 ═CH), 4.0 (m, 4H, CH2), 1.80 (m, 4H, CH2), 1.52 (m, 4H, CH2), 1.0 (t, J=7.5 Hz, 6H, CH3)13C NMR (CDCl3, 125.7 MHz) δppm: 159.1, 138.1, 135.7, 130.5, 130.4, 129.7, 129.4, 129.2, 128.0, 127.8, 126.2, 125.2, 124.7, 124.5, 124.3, 114.7, 67.7, 31.3, 19.2, 13.9.

Workup

  1. customAfter 2 hours the reaction was quenched by addition of 70 ml of methanol
  2. filtrationA light yellow solid was collected by filtration
  3. washwashed three times with methanol
  4. customto afford NMR-pure product in 2.36 g (84.5%)
  5. customyield

Sources & evidence

ORD record
ord-2faeeffc818d4b7e932b8911aaa0c42c
Source dataset
uspto-grants-2008_12
Patent number
US07459106B2

Reaction notes

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