Water → HCID 21299166, compound

HRID 34298Notes

Reaction equation

HRID 34298 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].C(OCC(=O)C[O:26][C:27]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)C1C=CC=CC=1)CCCCCCCCCCCCCCC.[OH2:47]>CCCCCC.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[CH2:4]([O:47][CH:41]([CH2:42][O:26][C:27]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH:40]=[CH2:27])[CH2:3][CH2:2][CH2:1][CH2:1][CH2:2][CH2:3][CH2:4][CH2:1][CH2:2][CH2:3][CH2:4][CH2:1][CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 3

HCID 962WaterHCID 212991621-Hexadecyloxy-3-triphenylmethoxypropan-2-oneHCID 178418339Butyllithium

Product 1

HCID 21299166HCID 21299166, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8058HexaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of n-butyllithium (47 ml, 113 mmol) in hexane was added to a suspension of methyltriphenylphosphonium bromide (40.0 g, 112 mmol) in 100 ml dry dioxane under N2 and the dark red solution was stirred at room temperature for 45 minutes. Compound 1 (35.1 g, 63.1 mmol) in 100 ml dry dioxane was added and the mixture was stirred for 2 hours. Water (10 ml) was added and the solution was partitioned between hexane and water. The aqueous layer was washed 2 times with hexane and the combined organic layers were dried over Na2SO4 and concentrated. The residue was crystallized from ethanol to afford 28.8 g (82%) of the title compound (2) as white needles, m.p. 34° ; NMR (CDCl3, (CH3)4Si); δ0.90 (t, 3H, J=6 Hz, --CH3), 1.25 (s, 26H, --CH2 --), 1.62 (m, 2H, --OCH2CH2R), 3.35 (t, 2H, J=7 Hz, --OCH2R), 3.62 (s, 2H, CH2OTr), 3.96 (s, 2 H, --CH2OR), 5.20 (d, 1 H, J=2 Hz, olefin), 5.40 (d, 1H, J=2 Hz, olefin), 7.2-7.5 (m, 15H, C(C6H5)85)3).

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. customthe solution was partitioned between hexane and water
  3. washThe aqueous layer was washed 2 times with hexane
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-1faf53b07d50474996f79a0d3787c674
Source dataset
uspto-grants-1988_08
Patent number
US04761404

Reaction notes

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