Pyridine → HCID 59333880, compound

HRID 1616779Notes

Reaction equation

HRID 1616779 reaction equation
CC1C=CC(S(Cl)(=O)=O)=CC=1.[CH2:12]([OH:20])[CH2:13][C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH3:19].N1C=CC=CC=1.CC1C=CC(S(OCCC#CCCCC)(=O)=O)=CC=1.[O:46]=[CH:47][C:48]1[CH:56]=[CH:55][C:53](O)=[C:50]([O:51][CH3:52])[CH:49]=1>C(Cl)Cl>[CH3:52][O:51][C:50]1[CH:49]=[C:48]([CH:56]=[CH:55][C:53]=1[O:20][CH2:12][CH2:13][C:14]#[C:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:47]=[O:46]

Participants

7

Reactant 5

HCID 1049PyridineHCID 1183VanillinHCID 73974-Toluenesulfonyl chlorideHCID 846943-Octyn-1-olHCID 13386678HCID 13386678, compound2×

Product 1

HCID 59333880HCID 59333880, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methylbenzenesulfonyl chloride (5.70 g, 30 mmol), 3-octyn-1-ol (1.52 mL, 20 mmol) and pyridine (3.24 mL, 40 mmol) in CH2Cl2 (20 mL) were treated according to Procedure 4 giving oct-3-ynyl 4-methylbenzenesulfonate (5.21 g, 93%) as a colourless oil. Vanillin (0.90 g, 5.94 mmol) was alkylated with oct-3-ynyl 4-methylbenzenesulfonate (2.50 g, 8.92 mmol) according to Procedure 4 and the crude product was recrystallised from purified by flash chromatography with 10% EtOAc/petrol as eluent to give 3-methoxy-4-(oct-3-ynyloxy)benzaldehyde (0.25 g, 16%) as a colourless crystalline solid; mp 64.5-65.5° C.; δH (400 MHz, CDCl3) 0.86 (t, J=7.2 Hz, 3H, CH3), 1.32-1.44 (m, 4H, CH3CH2CH2), 2.12 (t, J=7.2 Hz, 2H, CH2), 2.69 (t, J=7.2 Hz, 2H, CH2CH2O), 3.88 (s, 3H, OCH3), 4.15 (t, J=7.2 Hz, 2H, OCH2), 6.96 (d, J5,6=8.0 Hz, 1H, H5), 7.37 (s, 1H, H2), 7.39 (d, J5,6=8.0 Hz, 1H, H6), 9.80 (s, 1H, CHO); δC (100 MHz, CDCl3) 13.5, 18.3, 19.5, 21.8, 30.8, 55.9, 67.5, 74.8, 82.5, 109.4, 111.7, 126.4, 130.2, 149.7, 153.4, 190.7; vmax 1020, 1132, 1262, 1508, 1584, 1684, 2931 cm−1.

Workup

  1. customthe crude product was recrystallised
  2. customfrom purified by flash chromatography with 10% EtOAc/petrol as eluent

Sources & evidence

ORD record
ord-3d8414fdb59941aba7c7170c4e7900a1
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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