2-Bromoethanol → 2-Bromoethyl 5-(tetradecyloxy)furan-2-carboxylate

HRID 57209

Reaction equation

HRID 57209 reaction equation
[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([OH:23])=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[Br:24][CH2:25][CH2:26]O>CC(=O)OCC>[CH2:1]([O:15][C:16]1[O:20][C:19]([C:21]([O:23][CH2:26][CH2:25][Br:24])=[O:22])=[CH:18][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 108982-BromoethanolHCID 1151755-(Tetradecyloxy)-2-furoic acid

Product 1

HCID 498698992-Bromoethyl 5-(tetradecyloxy)furan-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared as described in Example 1 starting from 0.228 g (0.7 mmol) of 5-(tetradecyloxy)furan-2-carboxylic acid and 0.150 mL (2.1 mmol) of 2-bromoethanol. MS (m/z, ES+): 446.30 (79BrM+1, 100%), 448.30 (81BrM+1, 80%); 1H NMR (400 MHz, DMSO-d6) δ: 7.30 (d, 1H), 5.67 (d, 1H), 4.49 (t, 2H), 4.16 (t, 2H), 3.73 (t, 2H), 1.72 (p, 2H), 1.3-1.45 (m, 2H), 1.25 (s, 20H), 0.85 (t, 3H); EA found for C21H35BrO4: C, 58.93; H, 8.52; calcd: C, 58.47; H, 8.18.

Sources & evidence

ORD record
ord-7a14fb15a4214fa091f42d718bd63ae2
Source dataset
uspto-grants-2016_09
Patent number
US09434718B2

Linked notes

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