Ammonia → 12-fluoro-(E)-3-dodecen-1-ol

HRID 1263082Notes

Reaction equation

HRID 1263082 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][C:10]#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][F:20].[Na].N.[Cl-].[NH4+]>O1CCCC1>[F:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]/[CH:11]=[CH:10]/[CH2:9][CH2:8][OH:7]

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 25517Ammonium ChlorideHCID 5360545Sodium2×HCID 133725902-[(12-Fluorododec-3-YN-1-YL)oxy]oxane

Product 1

HCID 1337259312-fluoro-(E)-3-dodecen-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 12-fluoro-3-dodecyn-1-yl tetrahydropyranyl ether (1.42 g, 5 mmol) in dry tetrahydrofuran (50 ml.) is added slowly to a solution of sodium (920 mg., 40 mmol) in liquid ammonia (300 ml), the colour changing from blue through violet and red to a dull orange. More sodium (1.84 g, 80 mmol) is then added, the mixture becoming green then blue. The volume is increased to 500 ml. with liquid ammonia and the mixture stirred for two hours, after which dry ammonium chloride is added slowly until the color changed to pale yellow. After evaporation of the ammonia the residue is treated with dilute hydrochloric acid (6N., 50 ml.) and thoroughly extracted with ether. The neutral fraction is chromatographed on alumina (grade III, 30 g.). Elution with light petroleum yields 12-fluoro-(E)-3-dodecen-1-ol as a colourless oil, IR (film) 966 cm-1 (Trans C=C).

Workup

  1. temperatureThe volume is increased to 500 ml
  2. customAfter evaporation of the ammonia the residue
  3. additionis treated with dilute hydrochloric acid (6N., 50 ml.)
  4. extractionthoroughly extracted with ether
  5. customThe neutral fraction is chromatographed on alumina (grade III, 30 g.)
  6. washElution with light petroleum

Sources & evidence

ORD record
ord-b4e25db6c36b4276be00de7a9bcceecf
Source dataset
uspto-grants-1984_06
Patent number
US04455441

Reaction notes

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