Hydrochloric Acid → 2-Morpholinoethyl 5-(tetradecyloxy)furan-2-carboxylate

HRID 57221Notes

Reaction equation

HRID 57221 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[CH2:11]([O:25][C:26]1[O:30][C:29]([C:31]([OH:33])=[O:32])=[CH:28][CH:27]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>>[CH2:11]([O:25][C:26]1[O:30][C:29]([C:31]([O:33][CH2:3][CH2:4][N:5]2[CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)=[O:32])=[CH:28][CH:27]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 1151755-(Tetradecyloxy)-2-furoic acid

Product 1

HCID 498701632-Morpholinoethyl 5-(tetradecyloxy)furan-2-carboxylate

Procedure

The title compound was prepared as in Example 30 starting with 0.224 g (1.2 mmol) of 4-(2-chloroethyl)morpholine hydrochloride and 0.162 g (0.5 mmol) of 5-(tetradecyloxy)furan-2-carboxylic acid with the exception that a total of 0.730 g of cesium carbonate was added to neutralize the hydrochloride. 1H NMR (300 MHz, CDCl3) δ: 7.15 (d, 1H), 5.30 (d, 1H), 4.40 (t, 2H), 4.10 (t, 2H), 3.70 (app t, 4H), 2.70 (t, 2H), 2.55 (app t, 4H), 1.80 (p, 2H), 1.18-1.55 (m, 22H), 0.89 (t, 3H).

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-cdf47316cc2f4e77a399bd864378b626
Source dataset
uspto-grants-2016_09
Patent number
US09434718B2

Reaction notes

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