1-(triphenylmethyl)-1H-imidazole-4-carbaldehyde → HCID 59032668, compound

HRID 1883559Notes

Reaction equation

HRID 1883559 reaction equation
[C:1]1([C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]2[CH:12]=[C:11]([CH:13]=O)[N:10]=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-].[CH2:28]([O:35][CH2:36][CH2:37][CH2:38][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CC(C)([O-])C.[K+]>O1CCCC1>[C:29]1([CH2:28][O:35][CH2:36][CH2:37]/[CH:38]=[CH:13]\[C:11]2[N:10]=[CH:9][N:8]([C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:12]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 10929077(3-Benzyloxypropyl)triphenylphosphonium bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 59032668HCID 59032668, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
15 °C

Procedure

To a mechanically stirred solution of the aldehyde (16) (19.65 g, 58.1 mmol) in dry tetrahydrofuran (1 L), was added (3-benzyloxypropyl)triphenyl phosphonium bromide (30.02 g, 61.1 mmol). The resulting suspension was cooled to 15° C., and then a 1.0M solution (61.4 mL; 61.4 mmol) of potassium t-butoxide in tetrahydrofuran was added over five minutes. The reaction mixture was allowed to warm to room temperature and was stirred for 2 h. The reaction mixture was filtered through Celite; the filter cake was washed with tetrahydrofuran (2×150 mL); the filtrate and washings were combined, diluted with ether (800 mL) and refiltered through fresh Celite. The filtrate was concentrated under vacuum, and the residue was chromatographed on silica gel, eluting with a gradient of hexanes-ethyl acetate (3:1 to 2:1), to obtain the title compound (17) as a pale yellow powder, mp 101-104° C. MS(FAB) 471 (MH+).

Workup

  1. temperatureto warm to room temperature
  2. filtrationThe reaction mixture was filtered through Celite
  3. washthe filter cake was washed with tetrahydrofuran (2×150 mL)
  4. additiondiluted with ether (800 mL)
  5. concentrationThe filtrate was concentrated under vacuum
  6. customthe residue was chromatographed on silica gel
  7. washeluting with a gradient of hexanes-ethyl acetate (3:1 to 2:1)

Sources & evidence

ORD record
ord-de9736f1c3b9415ebc0993af24eeb533
Source dataset
uspto-grants-2004_07
Patent number
US06762186B2

Reaction notes

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