HCID 54096510, compound → 3,4-dihydro-2H-pyran

HRID 615207Notes

Reaction equation

HRID 615207 reaction equation
BrCC=CCCCCC.[O:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[O:16][CH2:17][CH:18]=[CH:19][CH2:20][C:21]#[CH:22]>>[O:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[O:16][CH2:17][CH:18]=[CH:19][CH2:20][C:21]#[CH:22].[O:10]1[CH:11]=[CH:12][CH2:13][CH2:14][CH2:15]1.[CH2:17]([OH:16])[CH:18]=[CH:19][CH2:20][C:21]#[CH:22]

Participants

5

Reactant 2

HCID 54096510HCID 54096510, compoundHCID 54428177HCID 54428177, compound

Product 3

HCID 80803,4-dihydro-2H-pyranHCID 54096510HCID 54096510, compoundHCID 56623977HCID 56623977, compound

Procedure

The 1-(tetrahydrofuranyloxy)-alka-2,8-dien-5-ynes are also prepared by the coupling reaction between a 1-haloalk-2-ene, for example, 1-bromooct-2-ene, the preparation of which is described in J. Chem. Soc., 3868 (1957) and 1-(tetrahydropyranyloxy)hex-2-en-5-yne. The coupling reaction is conducted in an aqueous or aqueous alcoholic solution, at a temperature of from 0° C. to about 100° C., optionally in the presence of a cuprous salt, for example, cuprous chloride, for from 1 to 24 hours. 1-(Tetrahydropyranyloxy)hex-2-en-5-yne is obtained by the acid-catalyzed reaction between dihydropyran and hex-2-en-5-yn-1-ol, the preparation of which is described in Bull. Soc. Chem. France, 2105 (1963). The reaction is conducted either without solvent or in the presence of an organic solvent such as ether or methylene chloride, in the presence of an acid catalyst such as sulphuric acid, hydrochloric acid or phosphorus oxychloride.

Workup

  1. customthe preparation of which
  2. customThe coupling reaction
  3. customof from 0° C. to about 100° C.
  4. customfor from 1 to 24 hours

Sources & evidence

ORD record
ord-be596e9c58214c1882916472f3487d02
Source dataset
uspto-grants-1985_02
Patent number
US04497827

Reaction notes

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