Acetaldehyde → HCID 11586634, compound

HRID 2053400Notes

Reaction equation

HRID 2053400 reaction equation
[Li]CCCC.[CH3:6][C@@H:7]([CH2:16][C:17]#[CH:18])[CH2:8][O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1.[CH:19](=[O:21])[CH3:20].[NH4+].[Cl-]>CCCCCC.C1COCC1.COC(C)(C)C>[CH3:6][C@H:7]([CH2:8][O:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1)[CH2:16][C:17]#[C:18][CH:19]([OH:21])[CH3:20]

Participants

8

Reactant 4

HCID 177AcetaldehydeHCID 25517Ammonium ChlorideHCID 16115994HCID 16115994, compoundHCID 178418339Butyllithium

Product 1

HCID 11586634HCID 11586634, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

2450 ml n-BuLi solution, 1.6 M, in hexane is added dropwise to a 650 g solution (3.566 mol) of (RS)-2-{[(S)-2-methylpent-4-in-1-yl]oxy}-3,4,5,6-tetrahydro-2H-pyrane (prepared in accordance with Ireland, Robert E. et al., Tetrahedron, 1997, 53, 39, 13221-13256.) in 325 ml of THF at −10° C. A solution of 310 g acetaldehyde in 1200 ml THF is then added dropwise. After 30 min., 3250 ml MTBE (methyl-tert.butylether) is added and 3250 ml 10% aq NH4Cl is added and further stirred for 10 min. The organic phase is washed twice with 1300 ml H2O each and concentrated in vacuo to dryness. 930 g of product is obtained. The obtained product is directly used in the subsequent step.

Workup

  1. washThe organic phase is washed twice with 1300 ml H2O each and
  2. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-56cd874ea3be474793571d18521fda7d
Source dataset
uspto-grants-2008_02
Patent number
US07326798B2

Reaction notes

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