Pyridine → HCID 53364295, compound

HRID 1616767Notes

Reaction equation

HRID 1616767 reaction equation
[CH3:1][C:2]1C=C[C:5](S(Cl)(=O)=O)=[CH:4][CH:3]=1.C(O)CCC#C.N1C=CC=CC=1.CC1C=CC(S(OCCCC#C)(=O)=O)=CC=1.[O:40]=[CH:41][C:42]1[CH:50]=[CH:49][C:47]([OH:48])=[C:44]([O:45][CH3:46])[CH:43]=1>C(Cl)Cl>[CH3:46][O:45][C:44]1[CH:43]=[C:42]([CH:50]=[CH:49][C:47]=1[O:48][CH2:5][CH2:4][CH2:3][C:2]#[CH:1])[CH:41]=[O:40]

Participants

7

Reactant 5

HCID 1049PyridineHCID 1183VanillinHCID 73974-Toluenesulfonyl chlorideHCID 793464-Pentyn-1-olHCID 10966564pent-4-ynyl tosylate2×

Product 1

HCID 53364295HCID 53364295, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methylbenzenesulfonyl chloride (5.7 g, 30 mmol), 4-pentyn-1-ol (1.8 mL, 20 mmol) and pyridine (3.2 mL, 40 mmol) in CH2Cl2 (20 mL) were treated according to Procedure 4 giving pent-4-ynyl 4-methylbenzenesulfonate (4.60 g, 97%) as a colourless oil. Vanillin (0.98 g, 6.4 mmol) was alkylated with pent-4-ynyl 4-methylbenzenesulfonate (2.3 g, 8.3 mmol) according to Procedure 4 and the crude product was recystallised from EtOAc/petrol to provide 3-methoxy-4-(pent-4-ynyloxy)benzaldehyde (1.25 g, 89%) as a colourless crystalline solid; mp 91-92° C.; δH (400 MHz, CDCl3) 1.98 (t, J=2.8 Hz, 1H, C≡CH), 2.09 (p, J=7.0 Hz, 2H, CH2), 2.43 (td, J=7.0, 2.8 Hz, 2H, CH2C≡CH), 3.91 (s, 3H, OCH3), 4.21 (t, J=7.0 Hz, 2H, OCH2), 6.99 (d, J5,6=8.0 Hz, 1H, H5), 7.40 (s, 1H, H2), 7.43 (d, J5,6=8.0 Hz, 1H, H6), 9.84 (s, 1H, CHO); δC (100 MHz, CDCl3) 15.1, 27.8, 56.0, 67.3, 69.1, 83.1, 109.3, 111.5, 126.7, 130.1, 149.9, 153.9, 190.8; vmax 1028, 1265, 1583, 1674, 2956, 3214 cm−1.

Sources & evidence

ORD record
ord-fabd14f1c48247d19e348166912ce03d
Source dataset
uspto-grants-2014_07
Patent number
US08765812B2

Reaction notes

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