Hept-6-ynal → 2-(Hex-5-ynyl)-5-isopropyl-1,3-oxathiane

HRID 346258Notes

Reaction equation

HRID 346258 reaction equation
[SH:1][CH2:2][CH:3]([CH:6]([CH3:8])[CH3:7])[CH2:4][OH:5].[CH:9](=O)[CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[CH:15]>>[CH2:14]([CH:15]1[S:1][CH2:2][CH:3]([CH:6]([CH3:8])[CH3:7])[CH2:4][O:5]1)[CH2:13][CH2:12][CH2:11][C:10]#[CH:9]

Participants

3

Reactant 2

HCID 11355455Hept-6-ynalHCID 133532852-Mercaptomethyl-3-methylbutan-1-ol

Product 1

HCID 199906302-(Hex-5-ynyl)-5-isopropyl-1,3-oxathiane

Procedure

Using the method described in Example 4(ii), and starting from 2-mercaptomethyl-3-methylbutan-1-ol and hept-6-ynal, 2-(hex-5-ynyl)-5-isopropyl-1,3-oxathiane was obtained as a mixture of isomers. Column chromatography on silica, eluting with hexane/ether gradients, gave a mixture of trans-and cis-isomers (50:50) followed by an enriched mixture of the trans-compound (95:5).

Sources & evidence

ORD record
ord-e5b3ae55a8b74c3e86d37636cb7330b4
Source dataset
uspto-grants-1991_10
Patent number
US05061726

Reaction notes

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