Water → HCID 12741940, compound

HRID 1579641Notes

Reaction equation

HRID 1579641 reaction equation
[CH3:1][C:2]1[C:10]2[O:11][CH:12]([C:14]([OH:16])=[O:15])[CH2:13][C:9]=2[C:8]2[CH2:7][CH:6]([CH2:17][CH2:18][CH3:19])[C:5](=[O:20])[C:4]=2[C:3]=1[CH3:21].[Br:22]Br.O.S(=O)(=O)(O)[O-].[Na+]>C(O)(=O)C>[CH3:1][C:2]1[C:10]2[O:11][CH:12]([C:14]([OH:16])=[O:15])[CH2:13][C:9]=2[C:8]2[CH2:7][C:6]([Br:22])([CH2:17][CH2:18][CH3:19])[C:5](=[O:20])[C:4]=2[C:3]=1[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 516919Sodium BisulfateHCID 12741936HCID 12741936, compound

Product 1

HCID 12741940HCID 12741940, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A stirred suspension of 4,5-dimethyl-6-oxo-7-propyl-1,2,7,8-tetrahydro-6H-indeno[5,4-b]furan-2-carboxylic acid (14 g., 0.00486 mole) in acetic acid (15 ml.) is treated with a solution of bromine (0.8 g., 0.005 mole) in acetic acid (5 ml.) during a three minute period. The reaction mixture is poured into water (100 ml.) containing sodium bisulfate (1 g.), extracted with ether, washed with water, dried over magnesium sulfate and the ether distilled at reduced pressure affording an oil which on trituration with cyclohexane affords 4,5-dimethyl-6-oxo-7-bromo-7-propyl-1,2,7,8-tetrahydro-6H-indeno[5,4-b]furan-2-carboxylic acid (1.4 g., 78%) as a white solid which melts at 78°C. and is used in the next step without further purification.

Workup

  1. extractionextracted with ether
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. distillationthe ether distilled at reduced pressure
  5. customaffording an oil which on trituration with cyclohexane

Sources & evidence

ORD record
ord-f6480b0c7c7d4f58a2f3a0442d305852
Source dataset
uspto-grants-1976_01
Patent number
US03931239

Reaction notes

Loading…