Ethanol → HCID 22722512, compound

HRID 1977967Notes

Reaction equation

HRID 1977967 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([O:13][C:14]1[CH:15]=[C:16]([CH:33]=[C:34]([CH3:36])[CH:35]=1)[O:17][CH2:18][CH2:19][CH2:20][O:21][N:22]1C(=O)C2=CC=CC=C2C1=O)(=[O:12])=[O:11])([O-:3])=[O:2].C(O)C.[BH4-].[Na+]>O1CCCC1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([O:13][C:14]1[CH:15]=[C:16]([CH:33]=[C:34]([CH3:36])[CH:35]=1)[O:17][CH2:18][CH2:19][CH2:20][O:21][NH2:22])(=[O:12])=[O:11])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 22722541HCID 22722541, compound

Product 1

HCID 22722512HCID 22722512, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of N-[3-[3-(2-nitrophenylsulfonyloxy)-5-methylphenoxy]propoxy]-phthalimide (2.33 g, 4.55 mmol), as prepared in the preceding step, in tetrahydrofuran (30 mL) and ethanol (30 mL) was treated with sodium borohydride (524 mg, 13.9 mmol). The reaction mixture was stirred at room temperature overnight, quenched carefully with 2N HCl (14 mL) and heated at 50° C. for 90 min. The reaction mixture was then concentrated to ¼ volume, basified with 2N NaOH, diluted with water, and extracted into ethyl acetate. The organic phase was dried (K2CO3) and purified by flash chromatography (1:4 to 1:2 diethyl ether/dichloromethane to give 1.12 g (64%) of the title compound as a pale yellow oil. 1H-NMR (300 MHz, CDCl3) δ7.98-8.01 (m, 1H), 7.79-7.87 (m, 2H), 7.66-7.74 (m, 1H), 6.64 (m, 1H), 6.60 (s, 1H), 6.57 (t, 1H, J=2 Hz), 3.96 (t, 2H, J=6 Hz), 3.80 (t, 2H, J=6 Hz), 2.27 (s, 3H), 2.02 (penet, 2H, J=6 Hz). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid) calcd. for C16H18N2O7S: 405.1 (M+Na). Found 405.2.

Workup

  1. customquenched carefully with 2N HCl (14 mL)
  2. temperatureheated at 50° C. for 90 min
  3. concentrationThe reaction mixture was then concentrated
  4. additiondiluted with water
  5. extractionextracted into ethyl acetate
  6. dry with materialThe organic phase was dried (K2CO3)
  7. custompurified by flash chromatography (1:4 to 1:2 diethyl ether/dichloromethane

Sources & evidence

ORD record
ord-3e532f5e0e2d4dc584b0f549865835ce
Source dataset
uspto-grants-2001_05
Patent number
US06235778B1

Reaction notes

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