5-Hexyn-1-ol → HCID 131729632, compound

HRID 1694591Notes

Reaction equation

HRID 1694591 reaction equation
I[C:2]1[CH:56]=[CH:55][C:5]([O:6][CH:7]2[CH2:18][N:17]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N+:28]([O-:30])=[O:29])(=[O:21])=[O:20])[CH2:16][CH2:15][CH2:14][N:13]([S:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[N+:40]([O-:42])=[O:41])(=[O:33])=[O:32])[CH2:12][CH2:11][CH2:10][N:9]([S:43]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[N+:52]([O-:54])=[O:53])(=[O:45])=[O:44])[CH2:8]2)=[CH:4][CH:3]=1.[CH2:57]([OH:63])[CH2:58][CH2:59][CH2:60][C:61]#[CH:62]>C1COCC1.C(N(CC)CC)C.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.[Cu]I>[OH:63][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][C:2]1[CH:56]=[CH:55][C:5]([O:6][CH:7]2[CH2:8][N:9]([S:43]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[N+:52]([O-:54])=[O:53])(=[O:44])=[O:45])[CH2:10][CH2:11][CH2:12][N:13]([S:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[N+:40]([O-:42])=[O:41])(=[O:32])=[O:33])[CH2:14][CH2:15][CH2:16][N:17]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[N+:28]([O-:30])=[O:29])(=[O:20])=[O:21])[CH2:18]2)=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 702345-Hexyn-1-olHCID 131729633HCID 131729633, compound

Product 1

HCID 131729632HCID 131729632, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

Compound 5b (250 mg, 0.26 mmol) and 5-hexyn-1-ol (43 μL, 0.39 mmol) were dissolved in the mixture of dry THF (6 mL) and triethylamine (2 mL) and the mixture was deaerated with argon. Pd(Ph3P)2Cl2 (3.6 mg, 0.005 mmol) and CuI (1.9 mg, 0.01 mmol) were added, and the mixture was stirred overnight at RT in dark. All volatiles were removed in vacuo. The residue was suspended in dichlormethane, washed twice with water and dried over Na2SO4. Purification on silica gel (eluent: MeOH: CH2Cl2, 1:9, v/v) yielded the title compound. 1H NMR (CDCl3): 7.99 (1H, m); 7.87 (2H, m); 7.78-7.57 (tot 9H); 7.29 (2H, d, J 8.8); 6.97 (2H, d, J 8.8); 5.12 (1H, m); 4.08 (2H, dd, J 4.6 and 15); 3.81-3.69 (tot 10H); 3.13 (2H, dd, J 5.1 and 15); 2.42 (2H, t, J 6.6); 1.78-1.63 (tot 4H); 1.32 (1H, t, J 4.7). ESI-TOF MS: required for C39H43N6O14S3+ (M+H)+ 915.19; found 915.24.

Workup

  1. customAll volatiles were removed in vacuo
  2. washwashed twice with water
  3. dry with materialdried over Na2SO4
  4. customPurification on silica gel (eluent: MeOH: CH2Cl2, 1:9, v/v)

Sources & evidence

ORD record
ord-c22fc1bf2e2f454c814e844f623a1ed0
Source dataset
uspto-grants-2012_04
Patent number
US08158782B2

Reaction notes

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