Tetrahydrofuran → HCID 86760553, compound

HRID 917364Notes

Reaction equation

HRID 917364 reaction equation
O1CCCC1.[F:6][C:7]([F:15])=[C:8]([CH3:14])[CH2:9][CH2:10][CH2:11][CH2:12][SH:13].[S:16]1[C:20]([C:21](Cl)=[O:22])=[CH:19][C:18]2[CH:24]=[CH:25][CH:26]=[CH:27][C:17]1=2.C(N(CC)CC)C>O>[S:16]1[C:20]([C:21](=[O:22])[S:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8]([CH3:14])=[C:7]([F:15])[F:6])=[CH:19][C:18]2[CH:24]=[CH:25][CH:26]=[CH:27][C:17]1=2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 142384Benzo[b]thiophene-2-carbonyl ChlorideHCID 23020242HCID 23020242, compound

Product 1

HCID 86760553HCID 86760553, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 10 ml of tetrahydrofuran were dissolved 0.25 g (1.5 mmol) of 6,6-difluoro-5-methyl-5-hexene-1-thiol and 0.39 g (2.0 mmol) of benzo[b]thiophene-2-carbonylchloride, followed by the drop-wise addition of 0.30 g (3.0 mmol) of triethylamine at room temperature, followed by stirring at the same temperature for 1 hour. The reaction liquid was then poured in water and extracted with diethyl ether. The organic layer was washed with water and a saturated saline solution in this order, followed by drying over anhydrous magnesium sulfate and concentration under reduced pressure. The residue was purified with silica gel column chromatography (diisopropyl ether:hexane=1:20) to obtain 0.39 g (yield: 80%) of S-(6,6-difluoro-5-methyl-5-hexenyl) benzo[b]thiophene-2-thiocarboxylate.

Workup

  1. customThe reaction liquid
  2. extractionextracted with diethyl ether
  3. washThe organic layer was washed with water
  4. dry with materialby drying over anhydrous magnesium sulfate and concentration under reduced pressure
  5. customThe residue was purified with silica gel column chromatography (diisopropyl ether:hexane=1:20)

Sources & evidence

ORD record
ord-1b1ea18222b7412aa1de274de4b314ed
Source dataset
uspto-grants-2007_09
Patent number
US07273878B2

Reaction notes

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