[(R)-2-(2,2-diethoxyethoxy)-4-pentenyloxymethyl]benzene → ({[(2R)-2-(2,2-diethoxyethoxy)hex-4-en-1-yl]oxy}methyl)benzene

HRID 1852516Notes

Reaction equation

HRID 1852516 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([OH:15])[CH2:11][CH:12]=[CH:13][CH3:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16]([O:18][CH:19]([O:35][CH2:36][CH3:37])[CH2:20]O[C@H](CC=C)COCC1C=CC=CC=1)[CH3:17]>>[CH2:16]([O:18][CH:19]([O:35][CH2:36][CH3:37])[CH2:20][O:15][C@H:10]([CH2:11][CH:12]=[CH:13][CH3:14])[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:17]

Participants

3

Reactant 2

HCID 59281174[(R)-2-(2,2-diethoxyethoxy)-4-pentenyloxymethyl]benzeneHCID 71352308(2R)-1-(benzyloxy)hex-4-en-2-ol

Product 1

HCID 86701081({[(2R)-2-(2,2-diethoxyethoxy)hex-4-en-1-yl]oxy}methyl)benzene

Procedure

(2R)-1-(Benzyloxy)hex-4-en-2-ol (C9) (150 g, 0.73 mol) was converted to the product according to the method used for synthesis of ({[(2R)-2-(2,2-diethoxyethoxy)pent-4-en-1-yl]oxy}methyl)benzene (C2) in Preparation P1, except that the initial combination of reagents was carried out at 0° C. The product was obtained as a brown oil (400 g, ≦0.73 mol), which was used for the next step without further purification. By 1H NMR analysis, this material contained a roughly 1:1 mixture of geometric isomers. 1H NMR (400 MHz, CDCl3), characteristic peaks for product: δ 7.25-7.38 (m, 5H), 5.38-5.60 (m, 2H), 4.55 and 4.55 (2 s, total 2H), 2.22-2.37 (m, 2H), 1.60-1.68 (m, 3H).

Workup

  1. customwas carried out at 0° C

Sources & evidence

ORD record
ord-f00f9478c5bf43a094a949e7b969cb15
Source dataset
uspto-grants-2015_02
Patent number
US08962616B2

Reaction notes

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