Hydrochloric Acid → (+)-(1r)-2-Pentyl-2-cyclopenten-1-ol

HRID 567392노트

반응식

HRID 567392 반응식
[CH2:1]([C:6]1[C:7](=[O:11])[CH2:8][CH2:9][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH3:5].O1CCBN1.CB1N2CCC[C@H]2C(C2C=CC=CC=2)(C2C=CC=CC=2)O1.S(C)C.Cl>O1CCCC1.C(OCC)C.CO>[CH2:1]([C:6]1[C@H:7]([OH:11])[CH2:8][CH2:9][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 1068Dimethyl SulfideHCID 1175492-Cyclopenten-1-one, 2-pentyl-HCID 2734713(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaboroleHCID 53628436CID 53628436

생성물 1

HCID 54447744(+)-(1r)-2-Pentyl-2-cyclopenten-1-ol수율 89%

시약·촉매·용매 3

HCID 887Methanol용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 2-pentyl-2-cyclopenten-1-one (9.12 g, 60 mmole) in 140 ml of tetrahydrofurane (THF) was treated with an oxazaborolidine represented above, namely (S)-tetrahydro-1-methyl-3,3-diphenyl-1 H,3 H-pyrrolo[1,2-c][1,3,2] oxazaborole (16.7 ml; 0.36 M in toluene, 6.0 mmole; see D. J. Mathre, ref. cited). A solution of BH3.S(CH3)2 (3.30 ml=2.64 g, 34.8 mmole) in THF (60 ml) was added dropwise at 0° over 1 h. The reaction was stopped with 3 ml of methanol (development of H2), followed by ethyl ether and 5% HCl. The organic phase, which had been washed to neutrality (2x with water and 1x with brine), was separated and the solvent evaporated. 9.5 g of a crude product were obtained, which was distilled in a bulb-to-bulb apparatus (oven temp. 60°/11 Pa), to give 8.1 g of (+)-(1 R)-2-pentyl-2-cyclopenten-1-ol (yield 89%).

후처리

  1. washThe organic phase, which had been washed to neutrality (2x with water and 1x with brine)
  2. customwas separated
  3. customthe solvent evaporated
  4. custom9.5 g of a crude product were obtained
  5. distillationwhich was distilled in a bulb-to-bulb apparatus (oven temp. 60°/11 Pa)

출처 및 근거

ORD 기록
ord-17e36990e44d423a8df2322db5d15c3b
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06177589B1

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