Water → HCID 135736093, compound

HRID 1921267Notes

Reaction equation

HRID 1921267 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[C:13]12([C:23]([C:26]3[C:31](O)=[CH:30][C:29]([OH:33])=[CH:28][C:27]=3[Cl:34])=[N:24][OH:25])[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[C:13]12([C:23]3[C:26]4[C:27]([Cl:34])=[CH:28][C:29]([OH:33])=[CH:30][C:31]=4[O:25][N:24]=3)[CH2:14][CH:15]3[CH2:16][CH:17]([CH2:18][CH:19]([CH2:21]3)[CH2:20]1)[CH2:22]2

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 136414661HCID 136414661, compound

Product 1

HCID 135736093HCID 135736093, compoundYield 24.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Diethylazodicarboxylate (0.92 g, 1.7 eq) in THF (20 ml) was added to a mixture of 1-adamantyl (2-chloro-4,6-dihydroxyphenyl)methanone oxime (1 g, 3.1 mmoles), triphenyl phosphine (1.4 g, 1.7 eq) in THF (20 ml) at 0° C. The mixture was stirred 2 h at 0° C., poured into water, extracted with ethylacetate, dried over Na2SO4 and concentrated under vacuum to give the crude product. Flash chromatography (AcOEt/toluene 1/9) and crystallisation from EtOH yielded the expected product (230 mg, 23%). mp 215° C.

Workup

  1. extractionextracted with ethylacetate
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customto give the crude product
  5. customFlash chromatography (AcOEt/toluene 1/9) and crystallisation from EtOH

Sources & evidence

ORD record
ord-ab484ee713e64dc89ab9264414ad7391
Source dataset
uspto-grants-2012_05
Patent number
US08173679B2

Reaction notes

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