Pyridine → HCID 59333853, compound

HRID 1616775Notes

Reaction equation

HRID 1616775 reaction equation
CC1C=CC(S(Cl)(=O)=O)=CC=1.[CH2:12]([OH:18])[CH2:13][C:14]#[C:15][CH2:16][CH3:17].N1C=CC=CC=1.CC1C=CC(S(OCCC#CCC)(=O)=O)=CC=1.[O:42]=[CH:43][C:44]1[CH:52]=[CH:51][C:49](O)=[C:46]([O:47][CH3:48])[CH:45]=1>C(Cl)Cl>[CH2:12]([O:18][C:49]1[CH:51]=[CH:52][C:44]([CH:43]=[O:42])=[CH:45][C:46]=1[O:47][CH3:48])[CH2:13][C:14]#[C:15][CH2:16][CH3:17]

Participants

7

Reactant 5

HCID 1049PyridineHCID 1183VanillinHCID 73974-Toluenesulfonyl chlorideHCID 660833-Hexyn-1-olHCID 14967550HCID 14967550, compound2×

Product 1

HCID 59333853HCID 59333853, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methylbenzenesulfonyl chloride (5.7 g, 30 mmol), 3-hexyn-1-ol (1.5 mL, 20 mmol) and pyridine (3.2 mL, 40 mmol) in CH2Cl2 (20 mL) were treated according to Procedure 4 giving hex-3-ynyl 4-methylbenzenesulfonate (3.8 g, 75%) as a colourless oil. Vanillin (0.76 g, 5.0 mmol) was alkylated with hex-3-ynyl 4-methylbenzenesulfonate (1.9 g, 7.5 mmol) according to Procedure 4 and the crude product was recrystallised from EtOAc/petrol to provide 4-(hex-3-ynyloxy)-3-methoxybenzaldehyde (0.45 g, 39%) as a colourless crystalline solid; mp 80-81° C.; δH (400 MHz, CDCl3) 1.12 (t, J=7.6 Hz, 3H, CH3), 2.17 (tq, J=7.6, 2.4 Hz, 2H, CH3CH2), 2.73 (tt, J=7.6, 2.4 Hz, 2H, OCH2CH2C), 3.92 (s, 3H, OCH3), 4.19 (t, J=7.6 Hz, 2H, OCH2), 7.00 (d, J5,6=8.0 Hz, 1H, H5), 7.41 (d, J2,6=1.6 Hz, 1H, H2), 7.44 (dd, J5,6=8.0, J2,6=1.6 Hz, 1H, H6), 9.85 (s, 1H, CHO); δC (100 MHz, CDCl3) 12.4, 14.0, 19.5, 56.0, 67.6, 74.3, 84.0, 109.5, 111.8, 126.6, 130.3, 149.9, 153.5, 190.8; vmax 1023, 1134, 1263, 1586, 1680, 2877, 2972 cm−1.

Workup

  1. customthe crude product was recrystallised from EtOAc/petrol

Sources & evidence

ORD record
ord-94212e2e586f4380a934f01566bc2005
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

Loading…