Triethylamine → HCID 54025454, compound

HRID 1274164Notes

Reaction equation

HRID 1274164 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([OH:12])=[C:8]2[C:3]=1[CH2:4][CH:5]([CH3:14])[CH2:6][C:7]2=[O:13].CCN(CC)CC.[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[Br:1][C:2]1[C:3]2[CH2:4][CH:5]([CH3:14])[CH2:6][C:7](=[O:13])[C:8]=2[C:9]([O:12][S:27]([C:23]2[S:22][CH:26]=[CH:25][CH:24]=2)(=[O:29])=[O:28])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 855182-Thiophenesulfonyl chlorideHCID 221203955-Bromo-3,4-dihydro-8-hydroxy-3-methyl-1(2H)-naphthalenone2×

Product 1

HCID 54025454HCID 54025454, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-8-hydroxy-3-methyl-1,2,3,4-tetrahydronaphthalen-1-one (Intermediate 1, Step 1) (0.2 g, 0.78 mmol) in DCM (10 mL) was added Et3N (1.1 mL, 7.8 mmol) and thiophene-2-sulphonyl chloride (0.57 g, 3.1 mmol). This mixture was stirred at room temperature for 5 h, and then partitioned with DCM (20 mL) and water (20 mL). The two phases were separated and the aqueous phase extracted with DCM (20 mL). The combined organic phases were dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel eluting with EtOAc:hexane (10:90-35:65) to afford the title compound (0.24 g, 75%) as an orange solid. mp 110-113° C. 1H NMR (360 MHz, CDCl3) δ 1.14(3H,d, J=6.0 Hz), 2.10-2.30(2H,m), 2.48-2.62(2H,m) 3.16-3.22(1H,m), 7.02(1H,d, J=8.7 Hz), 7.14(1H,dd, J=3.8, 4.9 Hz), 7.69-7.76(3H,m). MS(ES+) 401/403 (M+1).

Workup

  1. custompartitioned with DCM (20 mL) and water (20 mL)
  2. customThe two phases were separated
  3. extractionthe aqueous phase extracted with DCM (20 mL)
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. customevaporated
  6. customThe residue was chromatographed on silica gel eluting with EtOAc:hexane (10:90-35:65)

Sources & evidence

ORD record
ord-8ce7d7d80d874453bd06d57f00c130bc
Source dataset
uspto-grants-2000_12
Patent number
US06156761

Reaction notes

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