Hydrochloric Acid → 5-Oxo-1,3-oxathiolane-4-carboxylic acid p-methoxybenzyl ester

HRID 483105Notes

Reaction equation

HRID 483105 reaction equation
C([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.[O:21]=[C:22]1[O:26][CH2:25][S:24][CH2:23]1.Cl[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1)=[O:29].Cl>O1CCCC1>[CH3:39][O:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][O:30][C:28]([CH:23]2[C:22](=[O:21])[O:26][CH2:25][S:24]2)=[O:29])=[CH:33][CH:34]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 2724682Lithium diisopropylamideHCID 13305526Carbonochloridic acid, (4-methoxyphenyl)methyl esterHCID 134743731,3-Oxathiolan-5-oneHCID 178418339Butyllithium

Product 1

HCID 542385445-Oxo-1,3-oxathiolane-4-carboxylic acid p-methoxybenzyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of lithium diisopropylamide prepared from diisopropylamine (3.1 ml), n-butyllithium (14 ml as 1.6M hexane solution) and tetrahydrofuran (40 ml) is cooled at -70° C., mixed with 5-oxo-1,3-oxathiolane (1.04 g) and p-methoxybenzyl chloroformate. After 30 minutes, the mixture is acidified with hydrochloric acid, concentrated, and extracted with ethyl acetate. The extract is washed with water, dried, and concentrated to give 5-oxo-1,3-oxathiolane-4-carboxylic acid p-methoxybenzyl ester (265 mg).

Workup

  1. concentrationconcentrated
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ca5ae94f2b6347ffbca113c1151d9aea
Source dataset
uspto-grants-1986_03
Patent number
US04578378

Reaction notes

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