Tetrahydrofuran → 2-Methyl-3-hydroxy-4-mercaptomethyl-5-vinylpyridine

HRID 223547Notes

Reaction equation

HRID 223547 reaction equation
Cl.CC1C(O)=C(CN[C:12](=N)[SH:13])C(C=C)=CN=1.[O:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.CCO[CH2:25][CH3:26].[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+:34].O1[CH2:39][CH2:38]CC1>>[CH3:38][C:39]1[C:21]([OH:17])=[C:20]([CH2:12][SH:13])[C:19]([CH:25]=[CH2:26])=[CH:18][N:34]=1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 21868444Ether tetrahydrofuranHCID 178437128HCID 178437128, compound

Product 1

HCID 130669462-Methyl-3-hydroxy-4-mercaptomethyl-5-vinylpyridine

Procedure

The isothioureido compound from Example 25, Step A, (0.1 mole) in 200 ml. of tetrahydrofuran:ether (3:1 v/v) is added to excess lithium aluminum hydride under ether and nitrogen at 0° C. over 30 minutes. After stirring one hour at room temperature, it is poured into a mixture of tetrahydrofuran and saturated ammonium chloride solution. The water layer is separated and extracted with 2×400 ml. of tetrahydrofuran. The combined tetrahydrofuran solutions are dried and evaporated to dryness to give 2-methyl-3-hydroxy-4-mercaptomethyl-5-vinylpyridine.

Workup

  1. customThe water layer is separated
  2. extractionextracted with 2×400 ml
  3. dry with materialThe combined tetrahydrofuran solutions are dried
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-ab808fc495a84753b32b1df2c9a5c120
Source dataset
uspto-grants-1982_10
Patent number
US04355034

Reaction notes

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