Sulfuric Acid → HCID 14329712, compound

HRID 2231898Notes

Reaction equation

HRID 2231898 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH3:23])[CH2:10][CH2:9][C:8]2[C:11]([CH3:22])=[C:12]([O:17][CH2:18][CH2:19][CH2:20][OH:21])[C:13]([CH3:16])=[C:14]([CH3:15])[C:7]=2[O:6]1)=[O:4].[CH3:24][S:25](Cl)(=[O:27])=[O:26].S(=O)(=O)(O)O>C(Cl)Cl.C(N(CC)CC)C>[CH3:1][O:2][C:3]([C:5]1([CH3:23])[CH2:10][CH2:9][C:8]2[C:11]([CH3:22])=[C:12]([O:17][CH2:18][CH2:19][CH2:20][O:21][S:25]([CH3:24])(=[O:27])=[O:26])[C:13]([CH3:16])=[C:14]([CH3:15])[C:7]=2[O:6]1)=[O:4]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 31297Methanesulfonyl chlorideHCID 14329711HCID 14329711, compound

Product 1

HCID 14329712HCID 14329712, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 0.3 g of racemic-3,4-dihydro-2,5,7,8-tetramethyl-6-(3-hydroxypropoxy)-2H-1-benzopyran-2-carboxylic acid methyl ester in 5 ml of anhydrous methylene chloride and 0.33 ml of triethylamine was added 0.17 ml of methanesulfonyl chloride. The mixture was stirred at room temperature for 45 minutes then treated with 1N sulfuric acid and worked-up with methylene chloride in the usual manner. There was obtained 0.461 g of racemic-3,4-dihydro-2,5,7,8-tetramethyl-6-(3-methanesulfonyloxypropoxy)-2H-1-benzopyran-2-carboxylic acid methyl ester as an oil which was used without further purification.

Sources & evidence

ORD record
ord-7a01ce18bacc46a3b0701d7010650fde
Source dataset
uspto-grants-1988_11
Patent number
US04785017

Reaction notes

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