Methyl iodide → Methyl 2,2-bis(hydroxymethyl)pent-4-enoate

HRID 2190171Notes

Reaction equation

HRID 2190171 reaction equation
[OH:1][CH2:2][C:3]([CH2:10][OH:11])([CH2:7][CH:8]=[CH2:9])[C:4]([OH:6])=[O:5].[C:12]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[OH:1][CH2:2][C:3]([CH2:10][OH:11])([CH2:7][CH:8]=[CH2:9])[C:4]([O:6][CH3:12])=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 580523952,2-Bis(hydroxymethyl)pent-4-enoic acid

Product 1

HCID 58052417Methyl 2,2-bis(hydroxymethyl)pent-4-enoateYield 23.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of crude 2,2-bis(hydroxymethyl)pent-4-enoic acid (1 eq., 8.72 g), K2CO3 (3 eq., 22.9 g) and acetone (109 ml) was stirred at room temperature for 30 min. MeI (6 eq., 46.4 g) was added at 0° C. The mixture was stirred at room temperature for 2 days and concentrated. Water and EtOAc were added. The aqueous layer was extracted with 3×EtOAc. The organic layers were dried over MgSO4. Silica gel chromatography using 4-40% ACN (containing 5% MeOH)-DCM yields the title compound as colorless oil (2.2 g, 23% for two steps).

Workup

  1. stirringThe mixture was stirred at room temperature for 2 days
  2. concentrationconcentrated
  3. additionWater and EtOAc were added
  4. extractionThe aqueous layer was extracted with 3×EtOAc
  5. dry with materialThe organic layers were dried over MgSO4

Sources & evidence

ORD record
ord-6a321f27fe9f4a7fa730deb7a3933f77
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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