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Triphenylphosphine → (5R)-5-((tetrahydro-2H-pyran-2-yloxy)methyl)-4-oxaspiro[2.4]heptane

HRID 2068180
Notes
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Reaction equation

HRID 2068180 reaction equation
O[C@H:2]([CH2:9][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH2:3][CH2:4][C:5]1([OH:8])[CH2:7][CH2:6]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[O:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH:11]1[O:10][CH2:9][C@H:2]1[CH2:3][CH2:4][C:5]2([CH2:7][CH2:6]2)[O:8]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 67296674HCID 67296674, compound

Product 1

HCID 67296659(5R)-5-((tetrahydro-2H-pyran-2-yloxy)methyl)-4-oxaspiro[2.4]heptaneYield 69.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-((S)-3-hydroxy-4-(tetrahydro-2H-pyran-2-yloxy)butyl)-cyclopropanol (1.73 g, 0.0075 mol) and PPh3 (2.95 g, 0.0113 mol, Richjoint) in 32 mL of anhydrous THF at rt under N2 was added DEAD (1.96 g, 0.0113 mol, Aladdin) dropwise via a syringe. The reaction was stirred at 60° C. for 12 hours. The solvent was concentrated in vacuo. The red oil was purified by a silica gel column chromatography (8:1 (v/v) n-hexane/EtOAc) to give the title compound as colorless oil (1.1 g, 64%)2.

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. customThe red oil was purified by a silica gel column chromatography (8:1 (v/v) n-hexane/EtOAc)

Sources & evidence

ORD record
ord-22a66b17b5b04e79bdaec256619f6a72
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08293897B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes