Allyl Alcohol → HCID 86632152, compound

HRID 1967683Notes

Reaction equation

HRID 1967683 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:15](I)=[CH:14][C:3]=1/[CH:4]=[CH:5]/[C:6]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:13].[CH2:19]([OH:22])[CH:20]=[CH2:21]>>[CH3:13][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]([CH3:12])[C:6]=1/[CH:5]=[CH:4]/[C:3]1[CH:14]=[C:15]([CH2:21][CH2:20][CH:19]=[O:22])[CH:16]=[CH:17][C:2]=1[F:1]

Participants

3

Reactant 2

HCID 7858Allyl AlcoholHCID 68943433HCID 68943433, compound

Product 1

HCID 86632152HCID 86632152, compound

Procedure

(E)-2-(2-Fluoro-5-iodostyryl)-1,3-dimethylbenzene was coupled with allyl alcohol according to the method in Example 42. Purification by flash chromatography (40% CH2Cl2-hexanes) gave (E)-3-(3-(2,6-dimethylstyryl)-4-fluorophenyl)propanal as an oil. Yield (0.115 g, 52%): 1H NMR (400 MHz, DMSO-d6) δ 9.72 (t, J=1.2 Hz, 1H), 7.64 (dd, J=7.2, 2.4 Hz, 1H), 7.27 (d, J=16.8 Hz, 1H), 7.09-7.19 (m, 2H), 7.06 (s, 3H), 6.67 (d, J=16.8 Hz, 1H), 2.78-2.89 (m, 4H), 2.31 (s, 6H).

Workup

  1. customPurification by flash chromatography (40% CH2Cl2-hexanes)

Sources & evidence

ORD record
ord-76e3be48d4f744ceb0006307e6b1ddb7
Source dataset
uspto-grants-2013_04
Patent number
US08420863B2

Reaction notes

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