Propyne → 2,6,6-Trimethyl-1-[1-hydroxy-2-butynyl]-1,3-cyclohexadiene

HRID 1283357

反応式

HRID 1283357 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1[CH:10]=[O:11].[CH:12]#[C:13][CH3:14]>>[CH3:1][C:2]1[CH:7]=[CH:6][CH2:5][C:4]([CH3:8])([CH3:9])[C:3]=1[CH:10]([OH:11])[C:12]#[C:13][CH3:14]

参加物

3

反応物 2

HCID 6335PropyneHCID 61041Safranal

生成物 1

HCID 233380792,6,6-Trimethyl-1-[1-hydroxy-2-butynyl]-1,3-cyclohexadiene

実験手順

Safranal, prepared according to Compt. rend. 262, 1725 (1966), was reacted with propyne to give 2,6,6-trimethyl-1-[1-hydroxy-2-butynyl]-1,3-cyclohexadiene, following the procedure outlined in Example 18, paragraph b), for the reaction of citral with propyne. The above carbinol was oxidised with MnO2 to 2,6,6-trimethyl-1-tetrolyl-1,3-cyclohexadiene, following the procedure described in Example 18, paragraph c), for the oxidation of the dihydro analogue. The above acetylenic ketone was then partially reduced to the title compound following the method described in Example 18, paragraph a). Cis-2,6,6-trimethyl-1-crotonoyl-1,3-cyclohexadiene gave the following NMR data (CCl4): 1.06 (6 H, s), 1.69 (3 H, s), 2.09 (2 H, d, J = 2.3 cps), 2.14 (3 H, d, J = 5.5 cps), 5.81 (2 H, t + s, J = 2.3 cps), 6.2 (2 H, complex band) ppm (δ).

出典と根拠

ORDレコード
ord-a9a4fd584ca5443f8588808d878ac6d3
出典データセット
uspto-grants-1976_08
特許番号
US03975310

関連ノート

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