Propargyl bromide → HCID 53655826, compound

HRID 129069Notes

Reaction equation

[O:1]([C@H:9]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:10][C@@H:11]([OH:17])[CH2:12][C:13]([O:15][CH3:16])=[O:14])[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[CH2:35](Br)[C:36]#[CH:37]>>[O:1]([C@H:9]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:10][C@@H:11]([OH:17])[C@@H:12]([CH2:37][C:36]#[CH:35])[C:13]([O:15][CH3:16])=[O:14])[Si:2]([C:5]([CH3:6])([CH3:7])[CH3:8])([CH3:4])[CH3:3]

Participants

Reactant 2

HCID 7842Propargyl bromide

HCID 54058510HCID 54058510, compound

Product 1

HCID 53655826HCID 53655826, compound

Procedure

Analogously to Examples Cb) and c), methyl (3R,5R)-5-(t-butyldimethylsiloxy)-3-hydroxydocosanoate (Example Ib) was reacted with propargyl bromide to give methyl (2R,3R,5R)-5-(t-butyldimethylsiloxy)-3-hydroxy-2-(2-propynyl)docosanoate, IR (cm-1): 3310, 2120, 1740, 1255, the latter was saponified to give (2R,3R,5R)-5-(t-butyldimethylsiloxy)-3-hydroxy-2-(2-propinyl)-docosanoic acid, IR (cm-1): 3315, 2120, 1715, 1255, and this acid was cyclized to give (3R,4R)-4-[(R)-2-(t-butyldimethylsiloxy)nonadecyl]-3-(2-propynyl)-2-oxetanone, IR (cm-1): 3315, 2130, 1830, 1255.

Sources & evidence

ORD record: ord-3e64ee8ea5b04c659fb4ca3fb098aa8d
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05466708

Reaction notes

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