Hydrochloric Acid → HCID 73884446, compound

HRID 1278844Notes

Reaction equation

HRID 1278844 reaction equation
[Si](OCCCCCOCC1[C:17]([Se:30][C:31]#[C:32][C:33]([CH3:38])=[CH:34][C:35]([OH:37])=[O:36])=[CH:18][C:19]2[C:20]([CH3:29])([CH3:28])[CH2:21][CH2:22][C:23]([CH3:27])([CH3:26])[C:24]=2C=1)(C(C)(C)C)(C)C.[F-].[CH2:40]([N+](CCCC)(CCCC)CCCC)[CH2:41]CC.Cl.[CH2:58]([O:60][CH2:61][CH3:62])[CH3:59].[CH2:63]1C[O:66][CH2:65][CH2:64]1>>[OH:66][CH2:65][CH2:64][CH2:63][CH2:59][CH2:58][O:60][C:61]1[C:17]([Se:30][C:31]#[C:32][C:33]([CH3:38])=[CH:34][C:35]([O:37][CH2:40][CH3:41])=[O:36])=[CH:18][C:19]2[C:20]([CH3:28])([CH3:29])[CH2:21][CH2:22][C:23]([CH3:27])([CH3:26])[C:24]=2[CH:62]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 86587151HCID 86587151, compound

Product 1

HCID 73884446HCID 73884446, compound

Procedure

A mixture of the product of Example 43 (105 mg, 177 μmol), a 1M 1HF solution of tetra-n-butylammonium fluoride (770 μl) in THF is stirred at room temperature for 6 h. The reaction medium is treated with 1N HCl solution and ethyl ether. After separation of the phases by settling, the organic phase is washed with water, dried over anhydrous magnesium sulphate and concentrated. The product is purified by crystallization from a mixture of heptane and ethyl ether. Mass: 48 mg, yellowish powder. m.p.=134° C. 1H NMR/CDCl3: 1.18 to 1.29 (m, 14H); 1.56 to 1.68 (m, 8H); 1.83 (m, 2H); 2.42 (d, 3H); 3.69 (t, 2H); 4.02 (t, 2H); 6.08 (d, 1H); 6.72 (s, 1H); 7.54 (s, 1H).

Workup

  1. customAfter separation of the phases
  2. washthe organic phase is washed with water
  3. dry with materialdried over anhydrous magnesium sulphate
  4. concentrationconcentrated
  5. customThe product is purified by crystallization from a mixture of heptane and ethyl ether

Sources & evidence

ORD record
ord-5b60866978044264a1d135b18f9540d4
Source dataset
uspto-grants-2002_09
Patent number
US06444709B1

Reaction notes

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