1-Heptyne → HCID 20373764, compound

HRID 1415318Notes

Reaction equation

HRID 1415318 reaction equation
C([Li])CCC.[CH:6]#[C:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH:13]([CH:15]1[CH2:19][CH2:18][CH:17]([O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[CH:16]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[O:14]>CCCCCC.C1(C)C=CC=CC=1.CCOCC>[OH:14][CH:13]([CH:15]1[CH2:19][CH2:18][CH:17]([O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[CH:16]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])[C:6]#[C:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 3

HCID 123501-HeptyneHCID 20373753HCID 20373753, compoundHCID 178418339Butyllithium

Product 1

HCID 20373764HCID 20373764, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent2×HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

Under a nitrogen atmosphere at -40° C, a solution of 70.4 ml of n-butyl lithium in hexane (2.3 molar) is added dropwise to a solution of 1-heptyne (14.78 g, 2.2 equivalents) in 50 ml of toluene. The mixture is stirred at the same temperature for 10 minutes. The solution is transferred carefully to an addition funnel and added at to a solution of 2-formyl-5 -(tetrahydropyran-2-yloxy)-cyclopentaneheptanoic acid (22.82 g, 1 equivalent), described in Example 1, in 50 ml of toluene cooled to -70° C. The reaction is stirred at the same temperature for 2 hr. The mixture then is diluted with ether and washed with water. The aqueous layer is acidified with acetic acid and extracted with ether. The ether extract is washed with water, dried and concentrated to give the title compound, nmr (CDCl3) δ0.89 (+, 3H), 3.90 (broad, 1H), 4.33 (m, 1H).

Workup

  1. customThe solution is transferred carefully to an addition funnel
  2. stirringThe reaction is stirred at the same temperature for 2 hr
  3. washwashed with water
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washis washed with water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-26a6a9edf545470fb429caa025987627
Source dataset
uspto-grants-1977_01
Patent number
US04004027

Reaction notes

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