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(3-Bromoprop-1-yn-1-yl)benzene → 2-Methoxy-2-[3-(3-phenylprop-2-ynyloxy)phenyl]-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)but-1-yl methyl ether

HRID 654559
Notes
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Reaction equation

HRID 654559 reaction equation
[CH3:1][O:2][CH2:3][C:4]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([OH:24])[CH:19]=1)([O:16][CH3:17])[CH2:5][CH2:6][C:7]1([CH3:15])[O:12][CH2:11][C:10]([CH3:14])([CH3:13])[CH2:9][O:8]1.[C:25]1([C:31]#[C:32][CH2:33]Br)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH3:1][O:2][CH2:3][C:4]([O:16][CH3:17])([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:33][C:32]#[C:31][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:19]=1)[CH2:5][CH2:6][C:7]1([CH3:15])[O:8][CH2:9][C:10]([CH3:14])([CH3:13])[CH2:11][O:12]1
ParticipantsProcedureSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 10987157(3-Bromoprop-1-yn-1-yl)benzeneHCID 197615602-(3-Hydroxyphenyl)-2-methoxy-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)but-1-yl methyl ether

Product 1

HCID 197615472-Methoxy-2-[3-(3-phenylprop-2-ynyloxy)phenyl]-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)but-1-yl methyl etherYield 85%

Procedure

Using the procedure described in Example 12, 2-(3-hydroxyphenyl)-2-methoxy-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)but-1-yl methyl ether was reacted with 3-phenylprop-2-ynyl bromide to give 2-methoxy-2-[3-(3-phenylprop-2-ynyloxy)phenyl]-4-(2,5,5-trimethyl-1,3-dioxan-2-yl)but-1-yl methyl ether in 85% yield, as an oil.

Sources & evidence

ORD record
ord-a235f881b4e24bb5966e1e0739acd897
Source dataset
uspto-grants-1992_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05132328

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes