1-Bromoeicosane → HCID 15340538, compound

HRID 1684503Notes

Reaction equation

HRID 1684503 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[CH:18].C([Li])CCC.Br[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44]>C1COCC1.CN(C)P(=O)(N(C)C)N(C)C.CCCCCC>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[C:18][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH3:25]

Participants

7

Reactant 3

HCID 202711-BromoeicosaneHCID 1035662H-Pyran, tetrahydro-2-(10-undecyn-1-yloxy)-HCID 178418339Butyllithium

Product 1

HCID 15340538HCID 15340538, compoundYield 61.6%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

5 g (0.0198 mol) of 11-tetrahydropyranyloxyundecyne of Example 7 were placed in a mixture of 50 ml of THF and 25 ml of hexamethylphosphoric triamide under an argon atmosphere. At -60° C., 12.4 ml (0.0198 mol) of n-butyllithium in hexane were added dropwise. After 30 min at -60° C., a solution of 9.0 g (0.0248 mol) of 1-bromoeicosane in 25 ml of THF was added dropwise at -60° C. The mixture was left to warm up to room temperature. After 18 h at room temperature, it was poured into 25% aqueous NaH2PO4 solution and extracted with n-heptane (3×). The combined organic phases were dried (Na2SO4) and the solvent was removed. Flash chromatography on silica gel (n-heptane/ethyl acetate =15:1) gave 6.5 g (61.3% of theory) of 1-tetrahydropyranyloxy-hentriacont-10-yne.

Workup

  1. waitThe mixture was left
  2. waitAfter 18 h at room temperature
  3. extractionextracted with n-heptane (3×)
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-0fab22d819784f878b6e2afc57c65faa
Source dataset
uspto-grants-1997_06
Patent number
US05641767

Reaction notes

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