Acetone → HCID 14329713, compound

HRID 2231899Notes

Reaction equation

HRID 2231899 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH3:27])[CH2:10][CH2:9][C:8]2[C:11]([CH3:26])=[C:12]([O:17][CH2:18][CH2:19][CH2:20]OS(C)(=O)=O)[C:13]([CH3:16])=[C:14]([CH3:15])[C:7]=2[O:6]1)=[O:4].[I-:28].[Na+].CC(C)=O.O>CCOCC>[CH3:1][O:2][C:3]([C:5]1([CH3:27])[CH2:10][CH2:9][C:8]2[C:11]([CH3:26])=[C:12]([O:17][CH2:18][CH2:19][CH2:20][I:28])[C:13]([CH3:16])=[C:14]([CH3:15])[C:7]=2[O:6]1)=[O:4]

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 5238Sodium IodideHCID 14329712HCID 14329712, compound

Product 1

HCID 14329713HCID 14329713, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of the crude methanesulfonate from Example 14 (about 0.932 mmole), 595 mg of sodium iodide, and 5 ml of acetone was stirred at room temperature for 43.5 hours then treated with water and worked-up with ether in the usual manner (the ether extracts were additionally washed with dilute sodium bisulfite solution). The oily product (390 mg) was chromatographed on 20 g of silica gel. Elution with 19:1 and 9:1 hexane-ethyl acetate afforded 306 mg (76.0%) of racemic-3,4-dihydro-2,5,7,8-tetramethyl-6-(3-iodopropoxy)-2H-1-benzopyran-2-carboxylic acid methyl ester as a colorless oil. In another experiment, iodide prepared in this way crystallized to a solid, mp 73°-75.5° C.

Workup

  1. washwere additionally washed with dilute sodium bisulfite solution)
  2. customThe oily product (390 mg) was chromatographed on 20 g of silica gel
  3. washElution with 19:1 and 9:1 hexane-ethyl acetate

Sources & evidence

ORD record
ord-268f365824904e2699b8bf4f3794f0c5
Source dataset
uspto-grants-1988_11
Patent number
US04785017

Reaction notes

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