Tetrahydrofuran → HCID 10255676, compound

HRID 1744778Notes

Reaction equation

HRID 1744778 reaction equation
CCCCCCC.[N+:8]([CH2:11][C@:12]1([CH2:19][C:20]([O:22]CC)=[O:21])[CH2:18][C@@H:17]2[C@H:13]1[CH2:14][CH2:15][CH2:16]2)([O-:10])=[O:9].O1CCCC1.[OH-].[Na+]>O>[N+:8]([CH2:11][C@:12]1([CH2:19][C:20]([OH:22])=[O:21])[CH2:18][C@@H:17]2[C@H:13]1[CH2:14][CH2:15][CH2:16]2)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8900Heptane2×HCID 14798Sodium HydroxideHCID 59077271HCID 59077271, compound

Product 1

HCID 10255676HCID 10255676, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The n-heptane from the organic solution of the nitro ester of Example 7 (1.08 Kg; 4.49 mol) was replaced with tetrahydrofuran by azeotropic distillation at atmospheric pressure and constant volume. The solution was cooled to +25° C. and a solution of sodium hydroxide (0.359 Kg; 8.98 mol) in demineralised water (4.5 L) was added and the reaction stirred for 16 hours. n-Heptane (4.5 L) was added and the phases were separated. The aqueous phase was adjusted to pH 2–4 by the addition of concentrated hydrochloric acid (0.8 L) giving a suspension. The aqueous phase was extracted with ethyl acetate (9.6 L) to give the title product (0.928 Kg) in 97% yield as an organic solution which is used directly in the next step.

Workup

  1. temperatureThe solution was cooled to +25° C.
  2. customthe phases were separated
  3. additionThe aqueous phase was adjusted to pH 2–4 by the addition of concentrated hydrochloric acid (0.8 L)
  4. customgiving a suspension
  5. extractionThe aqueous phase was extracted with ethyl acetate (9.6 L)

Sources & evidence

ORD record
ord-e6ad6a196cc344e5ba87ac2ba2b98f53
Source dataset
uspto-grants-2006_03
Patent number
US07018818B2

Reaction notes

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