Ethylamine → HCID 86749180, compound

HRID 2260877Notes

Reaction equation

HRID 2260877 reaction equation
C(N)C.[CH3:4][Si:5]([C:8]#[CH:9])([CH3:7])[CH3:6].[CH2:10]([S:17]/[C:18](/I)=[CH:19]\[CH:20]=[C:21](/[S:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)\[Sn:22]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(Cl)Cl>C1C=CC=CC=1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:42]([S:41]/[C:21](/[Sn:22]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[CH:20]\[CH:19]=[C:18](\[S:17][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)/[C:9]#[C:8][Si:5]([CH3:7])([CH3:6])[CH3:4])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

8

Reactant 4

HCID 6341EthylamineHCID 6344DichloromethaneHCID 66111TrimethylsilylacetyleneHCID 9962290HCID 9962290, compound

Product 1

HCID 86749180HCID 86749180, compoundYield 86.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 241BenzeneSolvent

Procedure

A mixture of EtNH2 (1 mL) and trimethylsilylethyne (32 mL, 0.23 mmol) were added to a solution of 5 (0.148 g, 0.190 mmol), CuI (1.81 mg., 0.0095 mmol) and (Ph3P)2PdCl2 (6.67 mg, 0.0095 mmol) in benzene (3 mL) under argon. The resulting yellow-green solution was stirred at room temperature for 38 h, and then concentrated in vacuo. The residue was mixed with ether (20 mL) and water (5 mL), the layers were separated and the aqueous layer was extracted by ether (2×10 mL). The combined ether layers were washed with NH4Cl solution (2×25 mL) and water (10 mL), dried (MgSO4), and concentrated in vacuo. Flash column chromatography (1:6 CH2Cl2 :hexanes) of the dark, oily residue gave 7 as a yellow solid (122 mg, yield 86%): mp 122°-123° C.; 1H NMR δ 6.9-7.8 (m, 27 H), 4.06, 37.27, 0.03; Anal. Calcd for C41H40S2SiSn, C, 66.21; H, 5.42. Found, C, 66.42; H, 5.55.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was mixed with ether (20 mL) and water (5 mL)
  3. customthe layers were separated
  4. extractionthe aqueous layer was extracted by ether (2×10 mL)
  5. washThe combined ether layers were washed with NH4Cl solution (2×25 mL) and water (10 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3e66f5da968d4298b5f70aa727faf6ef
Source dataset
uspto-grants-1995_12
Patent number
US05478959

Reaction notes

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