Water → HCID 59421420, compound

HRID 1047108Notes

Reaction equation

HRID 1047108 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C@H:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:7][C@@H:8]2O)=[CH:4][CH:3]=1.S(Cl)([Cl:20])=O.O>O1CCCC1>[Cl:20][C@@H:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=2)[C@H:6]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 11521607(1S,3S)-6-chloro-3-phenylindan-1-ol

Product 1

HCID 59421420HCID 59421420, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (1S,3S)-6-chloro-3-phenylindan-1-ol (Va) (17 g) (synthesized as in example 8) in tetrahydrofuran (130 ml) is cooled with an ice bath. Thionyl chloride (9.9 g) in tetrahydrofuran (50 ml) is added drop wise at 4-5° C., and then the mixture is stirred over night at ambient temperature. A mixture of water and ice (approximately 25 ml) is added, and stirring is continued until all the ice has melted. The phases are separated, and the organic phase is washed twice with sodium bicarbonate (5% in water, 25 ml). The water phases are then combined, extracted with the organic phase, and then extracted with ethyl acetate (50 ml). The organic phases are then combined, dried with magnesium sulfate, filtered, and evaporated to dryness using a rotary evaporator. Yield 18.7 g (102%) of the title compound as an oil, which partly solidifies. The content of (1S,3R)-3,5-dichloro-1-phenylindan is 18% according to NMR.

Workup

  1. additionis added
  2. stirringstirring
  3. customThe phases are separated
  4. washthe organic phase is washed twice with sodium bicarbonate (5% in water, 25 ml)
  5. extractionextracted with the organic phase
  6. extractionextracted with ethyl acetate (50 ml)
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customa rotary evaporator

Sources & evidence

ORD record
ord-605389c0c7bc4e0fbb52ce0db8f98f34
Source dataset
uspto-grants-2013_10
Patent number
US08569499B2

Reaction notes

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