Tetrahydrofuran → HCID 23592306, compound

HRID 1611668Notes

Reaction equation

HRID 1611668 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[N:15]([CH:26]([CH3:32])CC(OC)=O)[S:16]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17].C1C[O:36][CH2:35]C1>>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([S:16]([N:15]([C:9]2[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=2[Cl:7])[C@H:26]([CH3:32])[CH2:35][OH:36])(=[O:18])=[O:17])=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran3×HCID 21226445Aluminium lithium hydrideHCID 22255712HCID 22255712, compound

Product 1

HCID 23592306HCID 23592306, compoundYield 98%

Conditions

Temperature
0 °C

Procedure

To a solution of LAH (18.5 mL of a 1M solution in THF, 18.5 mmol) in THF (50 mL) at −78° C. was added dropwise a solution of N-(2,5-dichlorophenyl)-N-(1-carbomethoxyprop-2-yl)-4-chlorobenzenesulfonamide (6.5 g, 15.4 mmol) in THF (100 mL). After the addition was complete, the reaction was briefly allowed to warm to 0° C. followed by cooling to −78° C. The suspension was quenched with 0.5N HCl (20 mL) and stirred at room temperature for 3 h. The resulting precipitate was removed by filteration and the filter cake washed well with Et2O. The filtrate was dried over MgSO4 and concentrated in vacuo to afford 4-chloro-N-(2,5-dichlorophenyl)-N-(1R)-(2-hydroxy-1-methylethyl)benzenesulfonamide as a white wax (5.88 g, 98% yield): 1H NMR (CDCl3) δ 7.77 (d, 2H, J=7.0 Hz), 7.34–7.52 (m, 5H), 4.27–4.42 (m, 1H), 3.35–3.61 (m, 2H), 1.77 (s, br, 1H), 1.05–1.09 (m, 3H).

Workup

  1. additionAfter the addition
  2. temperatureby cooling to −78° C
  3. customThe suspension was quenched with 0.5N HCl (20 mL)
  4. customThe resulting precipitate was removed by filteration
  5. washthe filter cake washed well with Et2O
  6. dry with materialThe filtrate was dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f353e95e4176493d9d2eb04a852c5cb9
Source dataset
uspto-grants-2006_01
Patent number
US06989399B2

Reaction notes

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