Sodium Cyanide → 5-Iodo-2-thiophenecarboxaldehyde

HRID 2165869Notes

Reaction equation

HRID 2165869 reaction equation
[C:1]([C:5]1([CH:9]=[O:10])[CH2:8][O:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[I:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1.[C-:21]#[N:22].[Na+]>C(OCC)C.O>[I:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([O-:7])=[O:17])=[CH:14][CH:13]=1.[C:1]([C:5]1([CH:9]([C:21]#[N:22])[OH:10])[CH2:8][O:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 8929Sodium CyanideHCID 743734-Iodobenzoyl chlorideHCID 140645973-tert-Butyloxetane-3-carbaldehyde

Product 2

HCID 36601035-Iodo-2-thiophenecarboxaldehydeHCID 23042573HCID 23042573, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 3-t-butyl-3-formyl-oxetane (1.0 g) and 4-iodobenzoyl chloride (2.6 g) in dry diethyl ether (35 ml), under nitrogen, was added a solution of sodium cyanide (1.25 g) in water (1.0 ml). The mixture was stirred overnight. The mixture was poured into water (50 ml.) and the aqueous mixture was extracted with diethyl ether. The ethereal solution was dried over anhydrous sodium sulphate and then evaporated in vacuo. The residue was chromatographed on silica pre-treated with triethylamine eluting with hexane:chloroform 1:3. The 4-iodobenzoate of 3-t-butyl-3-(cyano-hydroxymethyl)-oxetane was obtained as a colourless solid (2.54 g.). Nuclear magnetic resonance spectrum (NMR) was as follows: 1H (ppm from TMS in CDCl3, integral, number of peaks): 7.90-7.70, 4H, q; 5.80, 1H, s; 4.80-4.60, 4H, m; 1.10, 9H, s.

Workup

  1. extractionthe aqueous mixture was extracted with diethyl ether
  2. dry with materialThe ethereal solution was dried over anhydrous sodium sulphate
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica
  5. additionpre-treated with triethylamine eluting with hexane:chloroform 1:3

Sources & evidence

ORD record
ord-d69884de30f247d79984cb1594e5556e
Source dataset
uspto-grants-1990_07
Patent number
US04942173

Reaction notes

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