Diethyl Ether → 2,3-Dihydroxybutanedioate

HRID 1415565Notes

Reaction equation

HRID 1415565 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][CH2:6][CH:5]([NH:9][CH:10]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:17][C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:4]1)[CH3:2].C(OCC)C.[C:29]([OH:38])(=[O:37])[C@H:30]([C@@H:32]([C:34]([OH:36])=[O:35])[OH:33])[OH:31]>O1CCCC1>[CH2:1]([N:3]1[CH2:8][CH2:7][CH2:6][CH:5]([NH:9][CH:10]2[C:23]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:17][C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:4]1)[CH3:2].[C:34]([CH:32]([CH:30]([C:29]([O-:38])=[O:37])[OH:31])[OH:33])([O-:36])=[O:35]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 439655D-Tartaric acidHCID 21482860HCID 21482860, compound

Product 2

HCID 38061142,3-DihydroxybutanedioateHCID 21482860HCID 21482860, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.1 g. of N-(N-ethyl-3-piperidinyl)-9-xanthenylamine in 8 ml. of tetrahydrofuran and 50 ml. of diethyl ether at -5° C. was added 538 mg. of levo tartaric acid in 32 ml. of tetrahydrofuran. The resulting precipitate was allowed to stand one hour, filtered off, washed twice with 100 ml. portions of ether and air-dried to give N-(N-ethyl-3-piperidinyl)-9-xanthenylamine, tartrate, hydrate m.p. 146°-148° C. (dec.)

Workup

  1. filtrationfiltered off
  2. washwashed twice with 100 ml
  3. dry with materialportions of ether and air-dried

Sources & evidence

ORD record
ord-62658290c3b94d10b7f3f08112c3d9ea
Source dataset
uspto-grants-1977_01
Patent number
US04005208

Reaction notes

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