Formaldehyde → HCID 178484020, compound

HRID 967216Notes

Reaction equation

HRID 967216 reaction equation
[C:1]([O:5][C:6](=[O:20])[N:7]([CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([CH:16]=[C:17](Br)Br)[CH2:12][CH2:11]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[CH2:26]=[O:27]>O1CCCC1>[C:1]([O:5][C:6](=[O:20])[N:7]([CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]#[C:17][CH2:26][OH:27])[CH2:12][CH2:11]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 178418339ButyllithiumHCID 178484007HCID 178484007, compound

Product 1

HCID 178484020HCID 178484020, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 32.9 g (80 mmol) of trans-[4-(2,2-dibromo-vinyl)-cyclohexylmethyl]-methyl-carbamic acid tert-butyl ester in 640 ml tetrahydrofuran was treated at −78° C. with 105 ml (168 mmol) of n-butyl-lithium (ca 1.6 M in hexane). After 2 hours at this temperature, 24 g (800 mmol) of paraformaldehyde were added. The reaction mixture was warmed up to room temperature for 3 hours and after 0.5 hours at this temperature extracted with water/ether (3×). The organic phases were washed with aqueous 10% NaCl, dried over sodium sulfate and evaporated. Purification by flash-chromatography on silica gel (hexane/EtOAc 9:1 to 2:1) yielded 12.1 g (54%) of trans-[4-(3-hydroxy-prop-1-ynyl)-cyclohexylmethyl]-methyl-carbamic acid tert-butyl ester as orange viscous oil, MS: 282 (MH+).

Workup

  1. extractionextracted with water/ether (3×)
  2. washThe organic phases were washed with aqueous 10% NaCl
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customPurification by flash-chromatography on silica gel (hexane/EtOAc 9:1 to 2:1)

Sources & evidence

ORD record
ord-0bea73372ecb47ad92d436c63c1b010b
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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