Methanol → Dimethyl 2-[4-(hydroxymethyl)benzyl]-3-isopropylmaleate

HRID 1774403Notes

Reaction equation

[OH:1][CH2:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][C:8]2[C:9]([O:11][C:12](=O)C=2C(C)C)=[O:10])=[CH:5][CH:4]=1.CO.O1C[CH2:25][CH2:24][CH2:23]1.C[Si](C=[N+]=[N-])(C)C.CCCCCC.C1(C)C=CC=CC=1.[C:47]([O:50][CH2:51]C)(=[O:49])[CH3:48]>>[OH:1][CH2:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7]/[C:8](=[C:48](\[CH:24]([CH3:25])[CH3:23])/[C:47]([O:50][CH3:51])=[O:49])/[C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:4]=1

Participants

Reactant 5

HCID 887Methanol

HCID 8028Tetrahydrofuran

HCID 21584019Toluene ethylacetate

HCID 597065312-[4-(Hydroxymethyl)benzyl]-3-isopropylmaleic anhydride

HCID 86587183Trimethylsilyldiazomethane hexane

Product 1

HCID 66648450Dimethyl 2-[4-(hydroxymethyl)benzyl]-3-isopropylmaleateYield 81%

Procedure

To a solution of 2-[4-(hydroxymethyl)benzyl]-3-isopropylmaleic anhydride (101 mg, 0.388 mmol) in a mixed solvent of methanol (1.0 mL) and tetrahydrofuran (1.0 mL) was added a 2.0 M trimethylsilyl diazomethane-hexane solution (1.0 mL, 2.0 mmol) with stirring under ice cooling. The reaction mixture was stirred at room temperature for 2 h and directly concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography (toluene-ethyl acetate 4:1→3:1) to give 96 mg of dimethyl 2-[4-(hydroxymethyl)benzyl]-3-isopropylmaleate as oil (yield: 81%).

Workup

stirringThe reaction mixture was stirred at room temperature for 2 h
concentrationdirectly concentrated under reduced pressure
customThe residue thus obtained

Sources & evidence

ORD record: ord-8d963e04dc8641839ed8db629df2cafe
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260375B2

Reaction notes

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