1,3-Propanediol → HCID 22946319, compound

HRID 1698981Notes

Reaction equation

HRID 1698981 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 vaciio. 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 C18H24NO3Cl: 338 (M+H). Found: 338.

Workup

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

Sources & evidence

ORD record
ord-1ee1f56428f34c46a78f5c88fd8fe194
Source dataset
uspto-grants-2002_02
Patent number
US06344486B1

Reaction notes

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