Triethylamine → HCID 57522657, compound

HRID 1523000Notes

Reaction equation

HRID 1523000 reaction equation
[F:1][C:2]([F:24])([F:23])[S:3]([O:6][C:7]1[CH:12]=[C:11](I)[C:10](I)=[CH:9][C:8]=1[O:15][S:16]([C:19]([F:22])([F:21])[F:20])(=[O:18])=[O:17])(=[O:5])=[O:4].CCN([CH2:30][CH3:31])CC.[CH2:32]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:33][CH2:34][C:35]#[CH:36]>C1COCC1.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>[F:1][C:2]([F:24])([F:23])[S:3]([O:6][C:7]1[CH:12]=[C:11]([C:36]#[C:35][CH2:34][CH2:33][CH2:32][O:37][CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:10]([C:36]#[C:35][CH2:34][CH2:33][CH2:32][O:37][CH2:38][C:31]2[CH:30]=[CH:44][CH:39]=[CH:40][CH:41]=2)=[CH:9][C:8]=1[O:15][S:16]([C:19]([F:22])([F:21])[F:20])(=[O:18])=[O:17])(=[O:5])=[O:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 563055Benzene, [(4-pentynyloxy)methyl]-HCID 57522524HCID 57522524, compound

Product 1

HCID 57522657HCID 57522657, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A flame-dried 20 mL vial fitted with a screw-cap septa was charged with Pd(PPh3)2Cl2 (0.06 equiv., 0.12 mmol, 84 mg), Cut (0.12 equiv., 0.24 mmol, 45.6 mg), and 4,5-diiodo-1,2-phenylene bis(trifluoromethanesulfonate) (1 equiv., 2 mmol, 1.25 g). The vessel was evacuated and backfilled with nitrogen (3×), followed by the sequential addition of THF (4 mL), Et3N (3 equiv., 6 mmol, 0.85 mL), and ((pent-4-yn-1-yloxy)methyl)benzene (2.3 equiv., 4.6 mmol, 802 mg) in THF (1 mL). The reaction was stirred for 3 h at rt, filtered through a pad of silica and concentrated in vacuo. Purification by flash chromatography (step gradient from Hex to 10% EtOAc/Hex) afforded 4,5-bis(5-(benzyloxy)pent-1-yn-1-yl)-1,2-phenylene bis(trifluoromethanesulfonate) (1.14 g, 1.59 mmol, 79%). TLC Rf=0.27 (10% EtOAc/Hex); 1HNMR (600 MHz): δ 7.42 (s, 2H), 7.27-7.39 (10H), 4.56 (s, 4H), 3.65 (t, 4H, J=6.0 Hz), 2.62 (t, 4H, J=7.1 Hz), 1.92-1.98 (m, 4H); 13CNMR (150 MHz): δ 138.8, 138.3, 128.4, 128.2, 127.59, 127.56, 126.3, 121.7, 119.6, 117.5, 115.3, 98.1, 77.4, 73.0, 68.5, 28.6, 16.5; FTIR: 2859, 2230, 1489, 1433, 1210, 1178, 1135, 1080, 732 cm−1; HRMS-ESI: calc. for C32H28F6O8S2Na (M+Na)+: 741.1027. found: 741.1039.

Workup

  1. customA flame-dried 20 mL vial fitted with a screw-cap septa
  2. customThe vessel was evacuated
  3. filtrationfiltered through a pad of silica
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography (step gradient from Hex to 10% EtOAc/Hex)

Sources & evidence

ORD record
ord-6b8a9c9699394613a45e912a1860d7b8
Source dataset
uspto-grants-2015_07
Patent number
US09079835B2

Reaction notes

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