Water → HCID 15390710, compound

HRID 1099378Notes

Reaction equation

HRID 1099378 reaction equation
[CH2:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([OH:10])[C:4]=2[CH2:3][CH2:2]1.C(NC(C)C)(C)C.S(Cl)([Cl:21])(=O)=O.O>ClCCl>[Cl:21][C:6]1[CH:7]=[CH:8][C:9]2[CH2:1][CH2:2][CH2:3][C:4]=2[C:5]=1[OH:10]

Participants

6

Reactant 4

HCID 962WaterHCID 7912DiisopropylamineHCID 24648Sulfuryl chlorideHCID 742334-Hydroxyindan

Product 1

HCID 15390710HCID 15390710, compoundYield 12.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
22.5 °C

Procedure

To a clear solution of Indan-4-ol (40.0 gm, 0.297 mole) and Diisopropylamine (4.29 ml, 0.029 mole) in Dichloromethane (140 ml), a solution of Sulfuryl chloride (21.76 ml, 0.267 mole) in Dichloromethane (20 ml) was added at 0-5° C. The reaction mixture was stirred for 15 hours at 20-25° C. and poured into water (200 ml). Further it was extracted with Ethylacetate (2×200 ml). The organic layer was dried over Sodium sulphate, distilled under vacuum to give crude solid which was purified by column chromatography using Ethyl acetate:Hexane (2:98) as mobile phase. The collected fractions were distilled to give 5.7 gm of desired product as a solid.

Workup

  1. extractionFurther it was extracted with Ethylacetate (2×200 ml)
  2. dry with materialThe organic layer was dried over Sodium sulphate
  3. distillationdistilled under vacuum
  4. customto give crude solid which
  5. customwas purified by column chromatography
  6. distillationThe collected fractions were distilled

Sources & evidence

ORD record
ord-b5b2e0c95b9a46768ad2292345af33ef
Source dataset
uspto-grants-2012_03
Patent number
US08143424B2

Reaction notes

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