Triphenylphosphine → (2R)-Octan-2-yl 4-(benzyloxy)-3-fluorobenzoate

HRID 433045Notes

Reaction equation

HRID 433045 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([O:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][C:29]=1[F:37])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH3:38][C@H:39](O)[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45].N(C(OCC)=O)=NC(OCC)=O>C1COCC1.ClCCl>[CH2:20]([O:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([O:34][C@H:39]([CH3:38])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[O:33])=[CH:30][C:29]=1[F:37])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2723888(+)-2-OctanolHCID 187575074-(Benzyloxy)-3-fluorobenzoic acid

Product 1

HCID 70010782(2R)-Octan-2-yl 4-(benzyloxy)-3-fluorobenzoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Triphenylphosphine (7.92 g, 30 mmol) in THF (40 ml) was added dropwise to a stirred solution of compound 11 (7.00 g, 28 mmol), (S)-(+)-octan-2-ol (3.66 g 28 mmol) and diethyl azodicarboxylate (4.87 g, 28 mmol) in THF (100 ml). The reaction solution was left stirring under nitrogen until completion [reaction monitored by TLC (dichloromethane, silica)]. Upon completion, the solvent was removed in vacuo to yield a colourless solid which was purified by column chromatography (dichloromethane) on silica to yield a colourless oil. Yield 10.01 g (99%), [α]D=−22.4° at 25° C.

Workup

  1. waitThe reaction solution was left
  2. customUpon completion, the solvent was removed in vacuo
  3. customto yield a colourless solid which
  4. customwas purified by column chromatography (dichloromethane) on silica
  5. customto yield a colourless oil
  6. customat 25° C.

Sources & evidence

ORD record
ord-b140c9563e51415489f10104a8b8c2d7
Source dataset
uspto-grants-2003_12
Patent number
US06666989B1

Reaction notes

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