1,3-Propanediol → HCID 22946319, compound

HRID 1698854Notes

Reaction equation

HRID 1698854 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].[Cl:6][C:7]1[CH:8]=[C:9](O)[CH:10]=[C:11]([C:13]([N:15]([CH:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:16][CH:17]=[CH2:18])=[O:14])[CH:12]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[Cl:6][C:7]1[CH:12]=[C:11]([C:13]([N:15]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:16][CH:17]=[CH2:18])=[O:14])[CH:10]=[C:9]([O:4][CH2:3][CH2:2][CH2:1][OH:5])[CH:8]=1

Participants

5

Reactant 3

HCID 104421,3-PropanediolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22946320HCID 22946320, compound

Product 1

HCID 22946319HCID 22946319, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tetrahydrofuran (100 mL), 1,3-propanediol (1.6 mL, 30 mmol) and phenol 16 (4.3 g, 15 mmol) at 0° C. was added diethyl azodicarboxylate (DEAD, 3.6 mL, 23 mmol) dropwise over 10 min. The solution was warmed to ambient temperature and stirred for 16 h, prior to concentration in vacuo. The oil was partially purified by chromatography on silica gel to provide alcohol 17 (3.9 g) contaminated with Mitsunobu by-products. This material was used directly in subsequent experiments. 1H NMR (300 MHz, CDCl3) δ 6.93 (s, 2H), 6.8 (s, 1H), 5.9 (bs, 1H), 5.18 (d, 2H), 4.4-3.8 (m, 7H), 2.05 (m, 2H), 1.4-1.9 (m, 10H). Mass spectrum (CI) calcd. for C18 H24NO3Cl: 338 (M+H). Found: 338.

Workup

  1. concentrationto concentration in vacuo
  2. customThe oil was partially purified by chromatography on silica gel

Sources & evidence

ORD record
ord-0f90250d27fc40b8bf5567c209c0c0f2
Source dataset
uspto-grants-2002_02
Patent number
US06344466B2

Reaction notes

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