Bromomethyl 4-methoxyphenyl ketone → 2-(5-Benzyloxy-2-vinylphenoxy)-1-(4-methoxyphenyl)ethanone

HRID 254908Notes

Reaction equation

HRID 254908 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]2[CH:13]=[C:14](C3C=CC(OC)=CC=3)C[O:16][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Br[CH2:34][C:35]([C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1)=[O:36]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]([CH:13]=[CH2:14])=[C:11]([CH:10]=1)[O:16][CH2:34][C:35]([C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1)=[O:36])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 23665647Potassium tert-butoxideHCID 595921047-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran

Product 1

HCID 498213242-(5-Benzyloxy-2-vinylphenoxy)-1-(4-methoxyphenyl)ethanone

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

7-Benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran can be prepared according to the following reaction scheme and protocols. Referring to Scheme 1,4-benzyloxy-2-hydroxybenzaldehyde (compound 1) was reacted with a mixture of methyl triphenyl phosphonium bromide (MTPPB) and potassium tert-butoxide (t-BuOK), followed by reaction with 2-bromo-4′-methoxyacetophenone to give 2-(5-benzyloxy-2-vinylphenoxy)-1-(4-methoxyphenyl)ethanone (compound 2a), which was subsequently reacted with a mixture of MTPPB and t-BuOK to give 4-benzyloxy-2-[2-(4-methoxyphenyl)allyloxy]-1-vinylbenzene (compound 2). Reaction of compound 2 with Grubbs' catalyst (II) gives 7-benzyloxy-3(4-methoxyphenyl)-2H-1-benzopyran (compound 3).

Workup

  1. customaccording to the following reaction scheme and protocols

Sources & evidence

ORD record
ord-08c3f7a1947b4a5786710bea3bbfe1a7
Source dataset
uspto-grants-2011_01
Patent number
US07875736B2

Reaction notes

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