[(R)-2-(2,2-diethoxyethoxy)-4-pentenyloxymethyl]benzene → HCID 90253549, compound

HRID 1478719Notes

Reaction equation

HRID 1478719 reaction equation
[CH:1]1([C@H:4]([OH:9])[CH2:5]/[CH:6]=[CH:7]/[CH3:8])[CH2:3][CH2:2]1.[CH2:10]([O:12][CH:13]([O:29][CH2:30][CH3:31])[CH2:14]O[C@H](CC=C)COCC1C=CC=CC=1)[CH3:11]>>[CH2:10]([O:12][CH:13]([O:29][CH2:30][CH3:31])[CH2:14][O:9][C@@H:4]([CH:1]1[CH2:3][CH2:2]1)[CH2:5]/[CH:6]=[CH:7]/[CH3:8])[CH3:11]

Participants

3

Reactant 2

HCID 59281174[(R)-2-(2,2-diethoxyethoxy)-4-pentenyloxymethyl]benzeneHCID 90253544HCID 90253544, compound

Product 1

HCID 90253549HCID 90253549, compound

Procedure

(1R,3E)-1-Cyclopropylpent-3-en-1-ol (C24) was converted to the product according to the method used for the synthesis of ({[(2R)-2-(2,2-diethoxyethoxyl)pent-4-en-1-yl]oxy}methyl)benzene (C2) in Preparation P1, except that all reagents were combined at 0° C. The product was obtained as a colorless oil. Yield: 550 mg, 2.27 mmol, 48%. 1H NMR (400 MHz, CDCl3) δ 5.44-5.59 (m, 2H), 4.62 (dd, J=5.3, 5.3 Hz, 1H), 3.66-3.76 (m, 3H), 3.54-3.63 (m, 2H), 3.47 (dd, J=10.3, 5.5 Hz, 1H), 2.65 (dt, J=8.5, 5.9 Hz, 1H), 2.28-2.33 (m, 2H), 1.65-1.68 (m, 3H), 1.23 (t, J=7.1 Hz, 3H), 1.23 (t, J=7.0 Hz, 3H), 0.79-0.88 (m, 1H), 0.53-0.60 (m, 1H), 0.42-0.50 (m, 1H), 0.34-0.41 (m, 1H), 0.06-0.13 (m, 1H).

Workup

  1. customwere combined at 0° C
  2. customThe product was obtained as a colorless oil

Sources & evidence

ORD record
ord-093f2a2b0a2a40879797508b11948475
Source dataset
uspto-grants-2016_08
Patent number
US09403846B2

Reaction notes

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